Product Name

  • Name

    5-bromo-2-chloro-4’-ethoxydiphenylmethane

  • EINECS 636-921-5
  • CAS No. 461432-23-5
  • Article Data37
  • CAS DataBase
  • Density 1.371 g/cm3
  • Solubility
  • Melting Point
  • Formula C15H14BrClO
  • Boiling Point 392.976 °C at 760 mmHg
  • Molecular Weight 325.633
  • Flash Point 191.465 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 461432-23-5 (5-bromo-2-chloro-4’-ethoxydiphenylmethane)
  • Hazard Symbols
  • Synonyms 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene;4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene;
  • PSA 9.23000
  • LogP 5.09200

Synthetic route

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone
461432-22-4

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
With triethylsilane; boron trifluoride diethyl etherate In 1,2-dichloro-ethane; acetonitrile at 0 - 50℃; for 3h;97%
Stage #1: (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone With sodium tetrahydroborate In dichloromethane; acetonitrile at 30 - 40℃; for 0.5h;
Stage #2: With chloro-trimethyl-silane In dichloromethane; acetonitrile at 30 - 40℃; for 3h;
Stage #3: With boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 0 - 35℃; for 8h; Inert atmosphere;		96%
Stage #1: (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone With sodium tetrahydroborate In tetrahydrofuran at 10 - 15℃; for 0.5h; Inert atmosphere; Industry scale;
Stage #2: With aluminum (III) chloride In tetrahydrofuran at -5 - 70℃; for 20h; Inert atmosphere;
Stage #3: With water at 0 - 40℃; Inert atmosphere;		94%
4-(5-bromo-2-chlorobenzyl)phenol
864070-18-8

4-(5-bromo-2-chlorobenzyl)phenol

ethyl iodide
75-03-6

ethyl iodide

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone at 20℃;96%
4-bromo-1-chloro-2-(chloromethyl)benzene

4-bromo-1-chloro-2-(chloromethyl)benzene

Phenetole
103-73-1

Phenetole

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
With aluminum (III) chloride In ethyl acetate at 78℃; for 9h; Cooling with ice; Large scale;89%
5-bromo-2-amino-4'-ethoxydiphenylmethane

5-bromo-2-amino-4'-ethoxydiphenylmethane

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Stage #1: 5-bromo-2-amino-4'-ethoxydiphenylmethane With hydrogenchloride; sodium nitrite In water at -5 - 0℃; for 3h; Large scale;
Stage #2: With hydrogenchloride; copper(l) chloride In water at 20 - 80℃; for 4h; Large scale;		83%
Stage #1: 5-bromo-2-amino-4'-ethoxydiphenylmethane With hydrogenchloride; sodium nitrite In water at -5℃; for 3h; Industrial scale;
Stage #2: With copper(l) chloride In water at 20 - 80℃; for 4h; Industrial scale;		83%
Stage #1: 5-bromo-2-amino-4'-ethoxydiphenylmethane With hydrogenchloride; sodium nitrite In water at -5 - 0℃; for 3h; Large scale;
Stage #2: With hydrogenchloride; copper(l) chloride In water at 20 - 80℃; for 3h; Large scale;		79%
Phenetole
103-73-1

Phenetole

5-Bromo-2-chlorobenzyl bromide
149965-41-3

5-Bromo-2-chlorobenzyl bromide

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
With zinc(II) chloride at 75℃; for 6h;71%
(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone
461432-22-4

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
With potassium hydroxide; BF3.Et2O; Et3SiH In water; acetonitrile
5-bromo-2-chlorobenzoic acid
21739-92-4

5-bromo-2-chlorobenzoic acid

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 h / 20 °C
1.2: 3 h / 0 - 24 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 - 24 °C
View Scheme
Multi-step reaction with 3 steps
1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 20 °C
2: aluminum (III) chloride / dichloromethane / 1 h / -5 - 0 °C
3: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -20 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 2 h / Reflux
2: aluminum (III) chloride / dichloromethane / 1 h / Ca. -12 - Ca.-8 °C / Inert atmosphere
3: triethylsilane / dichloromethane / 0.3 h / 0 - 15 °C
View Scheme
Phenetole
103-73-1

Phenetole

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 h / 20 °C
1.2: 3 h / 0 - 24 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 - 24 °C
View Scheme
Multi-step reaction with 2 steps
1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 15 h / 25 - 30 °C
1.2: 2 h / 0 - 10 °C
2.1: aluminum (III) chloride; sodium tetrahydroborate / Dimethyl ether / 30 h / 0 - 65 °C
View Scheme
Multi-step reaction with 2 steps
1: aluminum (III) chloride / dichloromethane / -10 - 5 °C / Inert atmosphere
2: 1,1,3,3-Tetramethyldisiloxane / 5 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h
1.2: 1 h / 4 - 5 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 5 - 10 °C
View Scheme
Multi-step reaction with 2 steps
1: aluminum (III) chloride / dichloromethane / 1 h / -20 - 20 °C
2: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane; acetonitrile / 3 h / 0 - 50 °C
View Scheme
5-bromo-2-chloro-benzoyl chloride
21900-52-7

5-bromo-2-chloro-benzoyl chloride

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aluminum (III) chloride / dichloromethane / 1 h / -5 - 0 °C
2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -20 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: aluminum (III) chloride / dichloromethane / 1 h / Ca. -12 - Ca.-8 °C / Inert atmosphere
2: triethylsilane / dichloromethane / 0.3 h / 0 - 15 °C
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C
1.2: 0 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -10 - 20 °C
View Scheme
5-bromo-2-chlorobenzoic acid
21739-92-4

5-bromo-2-chlorobenzoic acid

Phenetole
103-73-1

Phenetole

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Stage #1: 5-bromo-2-chlorobenzoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 25 - 30℃; for 1h; Inert atmosphere;
Stage #2: Phenetole With aluminum (III) chloride In dichloromethane at 0 - 5℃; for 2h;
Stage #3: With triethylsilane In dichloromethane at 20 - 25℃; for 36h; Reagent/catalyst; Temperature;		2.5 g
4-Bromo-2-methylaniline
583-75-5

4-Bromo-2-methylaniline

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: copper(l) chloride; hydrogenchloride; sodium nitrite / water; 1,4-dioxane / 3.5 h / -5 - 80 °C
2: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 5 h / Reflux
3: zinc(II) chloride / 6 h / 75 °C
View Scheme
o-toluidine
95-53-4

o-toluidine

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0 °C
2: copper(l) chloride; hydrogenchloride; sodium nitrite / water; 1,4-dioxane / 3.5 h / -5 - 80 °C
3: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / chloroform / 5 h / Reflux
4: zinc(II) chloride / 6 h / 75 °C
View Scheme
5-bromo-2-chlorobenzoic acid
21739-92-4

5-bromo-2-chlorobenzoic acid

C8H12O

C8H12O

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 10 - 30 °C
1.2: 1 h / Cooling with ice
2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane; acetonitrile / 30 °C / Cooling with ice
View Scheme
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide; toluene / 2 h / 60 °C / Large scale
2.1: hydroxylamine hydrochloride / ethanol / 4 h / Reflux; Large scale
2.2: 5 h / Reflux; Large scale
3.1: hydrogenchloride; boron trichloride; calcium chloride / chlorobenzene / 20 h / 100 °C / Large scale
4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
4.2: 3 h / 20 - 80 °C / Large scale
5.1: lithium chloride; sodium tetrahydroborate / ethanol / 5 h / -5 - 70 °C / Large scale
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate; tetrabutylammomium bromide / 10 h / 130 °C / Industrial scale
2.1: palladium(II) hydroxide; hydrogen / ethanol / 6 h / Reflux; Industrial scale
3.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale
4.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale
5.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale
5.2: 4 h / 20 - 80 °C / Industrial scale
View Scheme
5-bromo-2-amino-4'-ethoxybenzophenone

5-bromo-2-amino-4'-ethoxybenzophenone

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
1.2: 3 h / 20 - 80 °C / Large scale
2.1: lithium chloride; sodium tetrahydroborate / ethanol / 5 h / -5 - 70 °C / Large scale
View Scheme
4-ethoxybenzonitrile
25117-74-2

4-ethoxybenzonitrile

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; boron trichloride; calcium chloride / chlorobenzene / 20 h / 100 °C / Large scale
2.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
2.2: 3 h / 20 - 80 °C / Large scale
3.1: lithium chloride; sodium tetrahydroborate / ethanol / 5 h / -5 - 70 °C / Large scale
View Scheme
4-ethoxybenzaldehyde
10031-82-0

4-ethoxybenzaldehyde

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydroxylamine hydrochloride / ethanol / 4 h / Reflux; Large scale
1.2: 5 h / Reflux; Large scale
2.1: hydrogenchloride; boron trichloride; calcium chloride / chlorobenzene / 20 h / 100 °C / Large scale
3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
3.2: 3 h / 20 - 80 °C / Large scale
4.1: lithium chloride; sodium tetrahydroborate / ethanol / 5 h / -5 - 70 °C / Large scale
View Scheme
Multi-step reaction with 4 steps
1.1: palladium(II) hydroxide; hydrogen / ethanol / 6 h / Reflux; Industrial scale
2.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale
3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale
4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale
4.2: 4 h / 20 - 80 °C / Industrial scale
View Scheme
4-bromo-aniline
106-40-1

4-bromo-aniline

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; boron trichloride; calcium chloride / chlorobenzene / 20 h / 100 °C / Large scale
2.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
2.2: 3 h / 20 - 80 °C / Large scale
3.1: lithium chloride; sodium tetrahydroborate / ethanol / 5 h / -5 - 70 °C / Large scale
View Scheme
Multi-step reaction with 4 steps
1.1: water; methanol / 5 h / 20 °C / Cooling with ice; Large scale
2.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale
3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale
4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
4.2: 4 h / 20 - 80 °C / Large scale
View Scheme
Multi-step reaction with 4 steps
1.1: water; methanol / 5.5 h / 20 °C / Cooling with ice; Industrial scale
2.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale
3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale
4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale
4.2: 4 h / 20 - 80 °C / Industrial scale
View Scheme
p-cresol
106-44-5

p-cresol

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide; toluene / 2.5 h / 60 °C / Large scale
2.1: N-chloro-succinimide; dibenzoyl peroxide / Petroleum ether / 8 h / Reflux; Large scale
3.1: zinc(II) chloride / ethyl acetate / 8 h / Reflux; Large scale
4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
4.2: 3 h / 20 - 80 °C / Large scale
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate; tetrabutylammomium bromide / 10 h / 130 °C / Large scale
2.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 6 h / Reflux; Large scale
3.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale
4.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale
5.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
5.2: 4 h / 20 - 80 °C / Large scale
View Scheme
1-ethoxy-4-methylbenzene
622-60-6

1-ethoxy-4-methylbenzene

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-chloro-succinimide; dibenzoyl peroxide / Petroleum ether / 8 h / Reflux; Large scale
2.1: zinc(II) chloride / ethyl acetate / 8 h / Reflux; Large scale
3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
3.2: 3 h / 20 - 80 °C / Large scale
View Scheme
Multi-step reaction with 4 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 6 h / Reflux; Large scale
2.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale
3.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale
4.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
4.2: 4 h / 20 - 80 °C / Large scale
View Scheme
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-Bromosuccinimide / dichloromethane / 10.5 h / 5 °C / Large scale
2: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Large scale
3: thionyl chloride / 3 h / 70 °C / Large scale
4: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale
View Scheme
2-chloro-5-bromobenzaldehyde
189628-37-3

2-chloro-5-bromobenzaldehyde

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Large scale
2: thionyl chloride / 3 h / 70 °C / Large scale
3: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale
View Scheme
5-bromo-2-chlorobenzyl alcohol
149965-40-2

5-bromo-2-chlorobenzyl alcohol

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 3 h / 70 °C / Large scale
2: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale
View Scheme
4-ethoxybenzyl bromide
2606-57-7

4-ethoxybenzyl bromide

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale
2.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale
3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
3.2: 4 h / 20 - 80 °C / Large scale
View Scheme
4-bromoacetanilide
103-88-8

4-bromoacetanilide

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride / ethyl acetate / 8 h / Cooling with ice; Reflux; Large scale
2.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale
3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
3.2: 4 h / 20 - 80 °C / Large scale
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale
2.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale
3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale
3.2: 4 h / 20 - 80 °C / Industrial scale
View Scheme
2'-(4-ethoxybenzyl)-4'-bromoacetanilide

2'-(4-ethoxybenzyl)-4'-bromoacetanilide

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Large scale
2.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
2.2: 4 h / 20 - 80 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale
2.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale
2.2: 4 h / 20 - 80 °C / Industrial scale
View Scheme
(2-chloro-5-bromophenyl)(4-fluorophenyl)methanone
915095-85-1

(2-chloro-5-bromophenyl)(4-fluorophenyl)methanone

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / N,N-dimethyl-formamide / 50 - 60 °C
2: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 10 °C / Inert atmosphere
View Scheme
fluorobenzene
462-06-6

fluorobenzene

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 39 - 42 °C
1.2: Reflux
2.1: sodium hydroxide / N,N-dimethyl-formamide / 50 - 60 °C
3.1: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 10 °C / Inert atmosphere
View Scheme
4-ethoxybenzyl alcohol
6214-44-4

4-ethoxybenzyl alcohol

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogen fluoride / ethyl acetate / 8.5 h / Cooling with ice; Industrial scale
2.1: hydrogenchloride / water; methanol / 6 h / 80 °C / Industrial scale
3.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 °C / Industrial scale
3.2: 4 h / 20 - 80 °C / Industrial scale
View Scheme
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

4-(5-bromo-2-chlorobenzyl)phenol
864070-18-8

4-(5-bromo-2-chlorobenzyl)phenol

Conditions
ConditionsYield
With boron tribromide; sodium hydrogencarbonate In dichloromethane at 20 - 30℃; for 0.5h; Inert atmosphere;100%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With boron trichloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: With boron tribromide In dichloromethane at 0℃;		98%
With boron tribromide In dichloromethane for 1h;95%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one
1461750-25-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one

C42H43ClO6

C42H43ClO6

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -80 - -75℃; for 3h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -80 - -75℃; for 4h;		100%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Sealed tube;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 1h; Sealed tube;
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

(2S,3R,4S,5R,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol

(2S,3R,4S,5R,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 5h; Inert atmosphere;		100%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-hexyllithium In tetrahydrofuran; hexane; toluene at -84 - -74℃; for 1h; Large scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -74 - -15℃; for 2h; Large scale;
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 5h;
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 5h;
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one

(3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one

(2S,3R,4S,5R,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol

(2S,3R,4S,5R,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-((trimethylsilyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 5h; Inert atmosphere;		100%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

(3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
461432-24-6

(3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane; toluene at -30℃; for 1h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene for 1h;		99%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; toluene at -78 - -70℃; for 0.5h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; toluene at -70℃; for 0.5h;
Stage #3: With methanesulfonic acid In methanol at 20℃; for 16h; Further stages.;		85%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

(3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol

(3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; toluene at -80 - -70℃; for 0.5h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; toluene at -80 - -70℃; for 1h;
Stage #3: With trifluoroacetic acid In tetrahydrofuran; water; toluene at -20 - 20℃;		98.4%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -80 - -78℃; for 0.5h; Inert atmosphere; Large scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene for 1h; Cooling; Large scale;
Stage #3: With trifluoroacetic acid In tetrahydrofuran; hexane; water; toluene at -30 - 15℃; for 2h; Large scale;
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

2-chloro-N-methoxy-N-methylacetamide
67442-07-3

2-chloro-N-methoxy-N-methylacetamide

2-chloro-1-(4-chloro-3-(4-ethoxybenzyl)phenyl)ethanone

2-chloro-1-(4-chloro-3-(4-ethoxybenzyl)phenyl)ethanone

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h;
Stage #2: 2-chloro-N-methoxy-N-methylacetamide In tetrahydrofuran; hexane at -78℃; for 3h;		98%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

A

2-chloro-4'-ethoxydiphenylmethane

2-chloro-4'-ethoxydiphenylmethane

B

1-benzyl-4-ethoxybenzene
35672-52-7

1-benzyl-4-ethoxybenzene

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In ethanol at 20℃; for 3h; Reagent/catalyst;A n/a
B 96%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

2-chloro-4'-ethoxydiphenylmethane

2-chloro-4'-ethoxydiphenylmethane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; toluene at -78℃; for 0.5h;93%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: With ammonium chloride In tetrahydrofuran at 20℃; for 0.5h;		93%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(3R,4R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5,5-difluorotetrahydro-2H-pyran-2-one
1369405-80-0

(3R,4R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5,5-difluorotetrahydro-2H-pyran-2-one

C42H41ClF2O6
1369406-03-0

C42H41ClF2O6

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere;
Stage #2: (3R,4R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5,5-difluorotetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -98℃; for 3h;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane; toluene at -98 - 20℃; stereoselective reaction;		91%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone
461432-22-4

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper(II) acetate monohydrate In water at 80℃; for 8h;90%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-thiopyran-2-one
131757-92-1

(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-thiopyran-2-one

2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-(4-ethoxybenzyl)phenyl]-5-thio-D-glucopyranose
1221506-04-2

2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-(4-ethoxybenzyl)phenyl]-5-thio-D-glucopyranose

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; Reflux;
Stage #2: (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-thiopyran-2-one In tetrahydrofuran at 20℃; for 1h; Grignard reaction;
Stage #3: With ammonium chloride In tetrahydrofuran; water Saturated solution;		89%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

C49H49ClO7

C49H49ClO7

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 0.5h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -78℃;		88%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

C19H25NO6

C19H25NO6

C30H31ClO6

C30H31ClO6

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With isopropylmagnesium chloride In tetrahydrofuran at -5 - 0℃; for 1h; Inert atmosphere;
Stage #2: C19H25NO6 In tetrahydrofuran at 25 - 30℃; Inert atmosphere;		88%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

2,3,4,5,6-penta-O-benzyl aldehydo D-glucose
78699-85-1

2,3,4,5,6-penta-O-benzyl aldehydo D-glucose

2-chloro-(1-methoxy-2,3,4,5,6-penta-benzyl-D-glucose)-2-ethoxydiphenylmethane

2-chloro-(1-methoxy-2,3,4,5,6-penta-benzyl-D-glucose)-2-ethoxydiphenylmethane

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1h;
Stage #2: 2,3,4,5,6-penta-O-benzyl-aldehydo-D-glucose In tetrahydrofuran; hexane at -70℃; for 2h;
Stage #3: With water In tetrahydrofuran; hexane at -70 - 20℃; for 20h;		87.1%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

2,3,4,6-Tetra-O-benzyl-D-glucopyranose
4291-69-4, 6386-24-9, 6564-72-3, 59531-24-7, 69257-52-9, 78184-89-1, 78609-16-2, 78609-17-3, 78609-18-4, 96553-53-6, 104111-61-7, 131347-08-5, 4132-28-9

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

2,3,4,6-tetrakis(benzyloxy)-1-(4-chloro-3-(4-ethoxybenzyl)phenyl)hexane-1,5-diol

2,3,4,6-tetrakis(benzyloxy)-1-(4-chloro-3-(4-ethoxybenzyl)phenyl)hexane-1,5-diol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With iodine; magnesium In tetrahydrofuran at 60℃; for 1h;
Stage #2: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose With isopropylmagnesium bromide In tetrahydrofuran at 0 - 60℃; for 2h;		87%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholin-4-yl)methanone
1103738-19-7

((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholin-4-yl)methanone

(4-chloro-3-(4-ethoxybenzyl)phenyl)((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolan-5-yl)methanone
1103738-30-2

(4-chloro-3-(4-ethoxybenzyl)phenyl)((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolan-5-yl)methanone

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran at -80 - -70℃; for 1h;
Stage #2: ((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholin-4-yl)methanone In tetrahydrofuran at -80 - 0℃;		86.3%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one
110391-10-1

(4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one

C50H49ClO6
1413373-21-3

C50H49ClO6

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With magnesium; ethylene dibromide In tetrahydrofuran for 1h; Inert atmosphere; Reflux;
Stage #2: (4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one In tetrahydrofuran at 25℃; for 3h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; water		86%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
461432-25-7

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With isopropylmagnesium chloride In tetrahydrofuran at -5 - 0℃; for 2h;
Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide With N,N,N,N,-tetramethylethylenediamine; isopropylmagnesium chloride; cobalt(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 30℃; for 2.5h; Reagent/catalyst; Solvent;		84%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; acetone at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide With copper(l) iodide In tetrahydrofuran at -40 - -30℃; for 1h; Reagent/catalyst; Temperature;
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

acetic anhydride
108-24-7

acetic anhydride

1-(4-chloro-3-(4-ethoxybenzyl)phenyl)ethanone

1-(4-chloro-3-(4-ethoxybenzyl)phenyl)ethanone

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With magnesium; methyl iodide In tetrahydrofuran for 1h; Reflux;
Stage #2: acetic anhydride In tetrahydrofuran at -20 - 20℃; for 3h;		84%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one

3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one

allyl alcohol
107-18-6

allyl alcohol

2-allyloxy-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-hydroxymethyI-tetrahydro-pyran-3,4,5-triol

2-allyloxy-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-hydroxymethyI-tetrahydro-pyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -80 - -70℃; for 1h;
Stage #2: 3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -80 - -70℃;
Stage #3: allyl alcohol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at -80 - -20℃;		83%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -80 - -70℃; for 1h;
Stage #2: 3,4,5-tris[(trimethylsilyl)oxy]-6-{[(trimethylsilyl)oxy]methyl}-tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -80 - -70℃;
Stage #3: allyl alcohol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at -80 - 20℃;
...Expand
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one
1431329-05-3

(2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one

(2R,3S,4S)-2,3,4-tribenzyloxy-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxanepent-4-yl)-1-(4-chloro-3-(4-ethoxybenzyl)phenyl)butan-1-one

(2R,3S,4S)-2,3,4-tribenzyloxy-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxanepent-4-yl)-1-(4-chloro-3-(4-ethoxybenzyl)phenyl)butan-1-one

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With isopropylmagnesium chloride In tetrahydrofuran at -5 - 0℃; for 1h; Inert atmosphere;
Stage #2: (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one In tetrahydrofuran at 20 - 30℃; Inert atmosphere;		83%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

C18H42O6Si4

C18H42O6Si4

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane; toluene at -78 - -65℃; for 2h; Inert atmosphere;78.6%
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78 - -68℃; for 1h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; n-heptane; cyclohexane at -78 - -68℃; for 30h;		78.3%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Large scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Large scale;		78%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere; Industrial scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With methanesulfonic acid In tetrahydrofuran; methanol; hexane; toluene at -78 - 40℃; for 14h; Industrial scale;		78%
Multi-step reaction with 2 steps
1.1: N,N,N',N'',N'''-pentamethyldiethylenetriamine; n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
1.2: 2 h / -78 °C / Inert atmosphere
2.1: methanol / 10 h / 20 °C
View Scheme
4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

methanesulfonic acid
75-75-2

methanesulfonic acid

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere; Large scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Large scale;
Stage #3: methanesulfonic acid In methanol at 0 - 40℃; for 11h; Large scale;		78%
...Expand
(4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one
79999-46-5, 72605-77-7

(4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene
461432-23-5

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

C42H43ClO6

C42H43ClO6

Conditions
ConditionsYield
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 0.5h;
Stage #2: (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -78℃; for 0.5h;		78%

4-(5-Bromo-2-chlorobenzyl)phenyl ethyl ether Specification

This chemical is called 4-Brom-1-chlor-2-(4-ethoxybenzyl)benzol, and its systematic name is 4-(5-bromo-2-chlorobenzyl)phenyl ethyl ether. With the molecular formula of C15H14BrClO, its molecular weight is 325.63. The CAS registry number of this chemical is 461432-23-5. Additionally, its product categories are Halides; Phenyls & Phenyl-Het.

Other characteristics of the 4-Brom-1-chlor-2-(4-ethoxybenzyl)benzol can be summarised as followings: (1)ACD/LogP: 5.73; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 1; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 9.23 Å2; (7)Index of Refraction: 1.584; (8)Molar Refractivity: 79.464 cm3; (9)Molar Volume: 237.48 cm3; (10)Polarizability: 31.502×10-24cm3; (11)Surface Tension: 41.059 dyne/cm; (12)Density: 1.371 g/cm3; (13)Flash Point: 191.465 °C; (14)Enthalpy of Vaporization: 61.77 kJ/mol; (15)Boiling Point: 392.976 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure: 
1.SMILES: Clc1c(cc(Br)cc1)Cc2ccc(OCC)cc2
2.InChI: InChI=1/C15H14BrClO/c1-2-18-14-6-3-11(4-7-14)9-12-10-13(16)5-8-15(12)17/h3-8,10H,2,9H2,1H3
3.InChIKey: ZUNCHZBITMUSRD-UHFFFAOYAH

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