Product Name

  • Name

    5-(2-Bromoethyl)-2,3-dihydrobenzofuran

  • EINECS 603-191-4
  • CAS No. 127264-14-6
  • Article Data19
  • CAS DataBase
  • Density 1.459 g/cm3
  • Solubility
  • Melting Point 65-67 °C
  • Formula C10H11BrO
  • Boiling Point 287.7 °C 760 mmHg
  • Molecular Weight 227.101
  • Flash Point 113.8°C
  • Transport Information
  • Appearance off-white powder
  • Safety
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 127264-14-6 (5-(2-Bromoethyl)-2,3-dihydrobenzofuran)
  • Hazard Symbols IrritantXi
  • Synonyms 2,3-dihydro-5-(2-bromoethyl)benzofuran;
  • PSA 9.23000
  • LogP 2.55890

Synthetic route

5-(2-hydroxyethyl)-2,3-dihydrobenzofuran
87776-76-9

5-(2-hydroxyethyl)-2,3-dihydrobenzofuran

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 63h;84%
With phosphorus tribromide In chloroform Reflux;75.9%
73%
2-bromo-1-(2,3-dihydrobenzofuran-5-yl)ethan-1-one
151427-19-9

2-bromo-1-(2,3-dihydrobenzofuran-5-yl)ethan-1-one

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Stage #1: 2-bromo-1-(2,3-dihydrobenzofuran-5-yl)ethan-1-one With sodium tetrahydroborate In tetrahydrofuran at 5 - 10℃; for 1h; Inert atmosphere;
Stage #2: With aluminum (III) chloride In tetrahydrofuran at 45 - 50℃; for 4h; Inert atmosphere;		74%
2-(2,3-dihydrobenzofuran-5-yl)ethylchloride
943034-50-2

2-(2,3-dihydrobenzofuran-5-yl)ethylchloride

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
With sodium bromide In acetone for 48h; Heating / reflux;
1-(2,3-dihydrobenzofuran-5-yl)ethanone
90843-31-5

1-(2,3-dihydrobenzofuran-5-yl)ethanone

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / methanol / 0.5 h / 0 - 5 °C
1.2: 6 h / 0 - 5 °C
2.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 5 - 10 °C / Inert atmosphere
2.2: 4 h / 45 - 50 °C / Inert atmosphere
View Scheme
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere
1.2: 0.5 h / 0 - 5 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / methanol / 0.5 h / 0 - 5 °C
2.2: 6 h / 0 - 5 °C
3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 5 - 10 °C / Inert atmosphere
3.2: 4 h / 45 - 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 10 °C
1.2: 10 - 20 °C
2.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 0 - 10 °C / Reflux
3.1: phosphorus tribromide / chloroform / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 10 °C
1.2: 10 - 20 °C
2.1: water; sodium hydroxide / 20 °C
3.1: hydrazine hydrate; sodium hydroxide / 90 - 100 °C
4.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 0 - 10 °C / Reflux
5.1: phosphorus tribromide / chloroform / Reflux
View Scheme
2-chloro-1-(2,3-dihydrobenzofuran-5-yl)ethanone
64089-34-5

2-chloro-1-(2,3-dihydrobenzofuran-5-yl)ethanone

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; sulfuric acid / tetrahydrofuran / 10 h / -5 - 0 °C
2: sodium bromide / acetone / 48 h / Heating / reflux
View Scheme
ethyl 2( 2,3-dihydro-1-benzofuran-5-yl)oxoacetate
79002-49-6

ethyl 2( 2,3-dihydro-1-benzofuran-5-yl)oxoacetate

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: water; sodium hydroxide / 20 °C
2: hydrazine hydrate; sodium hydroxide / 90 - 100 °C
3: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 0 - 10 °C / Reflux
4: phosphorus tribromide / chloroform / Reflux
View Scheme
C10H7O4(1-)*Na(1+)

C10H7O4(1-)*Na(1+)

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrazine hydrate; sodium hydroxide / 90 - 100 °C
2: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 0 - 10 °C / Reflux
3: phosphorus tribromide / chloroform / Reflux
View Scheme
2,3-dihydrobenzofuran-5-acetic acid
69999-16-2

2,3-dihydrobenzofuran-5-acetic acid

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 0 - 10 °C / Reflux
2: phosphorus tribromide / chloroform / Reflux
View Scheme
4-hydroxyphenylacetate
156-38-7

4-hydroxyphenylacetate

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: potassium iodide; sodium hydroxide / dimethyl sulfoxide / 50 - 80 °C
2: toluene-4-sulfonic acid / Reflux; Large scale
3: polyphosphoric acid / toluene / 105 - 110 °C
4: sodium hydroxide; water / methanol / 25 - 30 °C
5: sodium hydroxide; hydrogen / methanol; water / 60 - 65 °C / 6080.41 - 7600.51 Torr
6: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
7: phosphorus tribromide / chloroform / Reflux
View Scheme
Multi-step reaction with 7 steps
1: potassium iodide; sodium hydroxide / dimethyl sulfoxide / 50 - 80 °C
2: toluene-4-sulfonic acid / Reflux; Large scale
3: polyphosphoric acid / toluene / 105 - 110 °C
4: hydrogen; acetic acid; palladium 10% on activated carbon / methanol / 65 - 70 °C / 3040.2 - 3800.26 Torr
5: sodium hydroxide; water / methanol / 25 - 60 °C
6: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
7: phosphorus tribromide / chloroform / Reflux
View Scheme
4-((2,2-dimethoxy)ethoxy)phenylacetic acid

4-((2,2-dimethoxy)ethoxy)phenylacetic acid

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: toluene-4-sulfonic acid / Reflux; Large scale
2: polyphosphoric acid / toluene / 105 - 110 °C
3: hydrogen; acetic acid; palladium 10% on activated carbon / methanol / 65 - 70 °C / 3040.2 - 3800.26 Torr
4: sodium hydroxide; water / methanol / 25 - 60 °C
5: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
6: phosphorus tribromide / chloroform / Reflux
View Scheme
Multi-step reaction with 6 steps
1: toluene-4-sulfonic acid / Reflux; Large scale
2: polyphosphoric acid / toluene / 105 - 110 °C
3: sodium hydroxide; water / methanol / 25 - 30 °C
4: sodium hydroxide; hydrogen / methanol; water / 60 - 65 °C / 6080.41 - 7600.51 Torr
5: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
6: phosphorus tribromide / chloroform / Reflux
View Scheme
methyl 4-((2,2-dimethoxy)ethoxy)phenylacetate

methyl 4-((2,2-dimethoxy)ethoxy)phenylacetate

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: polyphosphoric acid / toluene / 105 - 110 °C
2: hydrogen; acetic acid; palladium 10% on activated carbon / methanol / 65 - 70 °C / 3040.2 - 3800.26 Torr
3: sodium hydroxide; water / methanol / 25 - 60 °C
4: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
5: phosphorus tribromide / chloroform / Reflux
View Scheme
Multi-step reaction with 5 steps
1: polyphosphoric acid / toluene / 105 - 110 °C
2: sodium hydroxide; water / methanol / 25 - 30 °C
3: sodium hydroxide; hydrogen / methanol; water / 60 - 65 °C / 6080.41 - 7600.51 Torr
4: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
5: phosphorus tribromide / chloroform / Reflux
View Scheme
methyl 2-(benzofuran-5-yl)acetate
121638-36-6

methyl 2-(benzofuran-5-yl)acetate

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide; water / methanol / 25 - 30 °C
2: sodium hydroxide; hydrogen / methanol; water / 60 - 65 °C / 6080.41 - 7600.51 Torr
3: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
4: phosphorus tribromide / chloroform / Reflux
View Scheme
Multi-step reaction with 4 steps
1: hydrogen; acetic acid; palladium 10% on activated carbon / methanol / 65 - 70 °C / 3040.2 - 3800.26 Torr
2: sodium hydroxide; water / methanol / 25 - 60 °C
3: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
4: phosphorus tribromide / chloroform / Reflux
View Scheme
benzofuran-5-yl-acetic acid
142935-60-2

benzofuran-5-yl-acetic acid

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide; hydrogen / methanol; water / 60 - 65 °C / 6080.41 - 7600.51 Torr
2: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
3: phosphorus tribromide / chloroform / Reflux
View Scheme
methyl 2-(2,3-dihydrobenzofuran-5-yl)acetate
155852-41-8

methyl 2-(2,3-dihydrobenzofuran-5-yl)acetate

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide; water / methanol / 25 - 60 °C
2: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 10 °C / Reflux
3: phosphorus tribromide / chloroform / Reflux
View Scheme
styrene
292638-84-7

styrene

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

1-benzyl-4-iodo-5-methylpyridin-2(1H)-one

1-benzyl-4-iodo-5-methylpyridin-2(1H)-one

(E)-1-benzyl-3-(2-(2,3-dihydrobenzofuran-5-yl)ethyl)-5-methyl-4-styrylpyridin-2(1H)-one

(E)-1-benzyl-3-(2-(2,3-dihydrobenzofuran-5-yl)ethyl)-5-methyl-4-styrylpyridin-2(1H)-one

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In 1,4-dioxane at 105℃; for 36h; Inert atmosphere;96%
...Expand
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

bromobenzene
108-86-1

bromobenzene

5-(1-phenylethyl)-2,3-dihydrobenzofuran

5-(1-phenylethyl)-2,3-dihydrobenzofuran

Conditions
ConditionsYield
With nickel(II) iodide; Bathocuproine; tetrabutylammomium bromide; zinc at 20℃; regioselective reaction;95%
With nickel(II) bromide dimethoxyethane; [Ir(dF(CF3)ppy)2(phen)]PF6; Bathocuproine; diisopropylamine; magnesium bromide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; Irradiation; regioselective reaction;87%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

(S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate

(S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium hydroxide; triethylmethylammonium chloride In water; toluene at 100℃; for 15.25h;
Stage #2: With hydrogen bromide In water; toluene Product distribution / selectivity;		93.2%
Stage #1: (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium hydroxide; triethylmethylammonium chloride In 2-methyltetrahydrofuran; water at 60 - 70℃;
Stage #2: 2,3-dihydro-5-(2-bromoethyl)benzofuran In 2-methyltetrahydrofuran; water for 16h; Heating / reflux;
Stage #3: With hydrogen bromide In 2-methyltetrahydrofuran; water at 0 - 20℃; for 2h; Product distribution / selectivity;		90.67%
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium hydroxide; triethylmethylammonium chloride In water; butanone at 75℃; for 6h;
Stage #2: With hydrogen bromide In water; butanone at 0 - 5℃; for 2h; Product distribution / selectivity;		84.92%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

4-Bromodiphenyl ether
101-55-3

4-Bromodiphenyl ether

C22H20O2

C22H20O2

Conditions
ConditionsYield
With nickel(II) iodide; Bathocuproine; tetrabutylammomium bromide; zinc at 20℃; regioselective reaction;90%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

C18H17NO

C18H17NO

Conditions
ConditionsYield
With nickel(II) iodide; Bathocuproine; tetrabutylammomium bromide; zinc at 20℃; regioselective reaction;90%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

3-(S)-(+)-(1-cyano-1,1-diphenylmethyl)pyrrolidine hydrobromide

3-(S)-(+)-(1-cyano-1,1-diphenylmethyl)pyrrolidine hydrobromide

(-)-3S-(1-carbonitrile-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine hydrobromide

(-)-3S-(1-carbonitrile-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine hydrobromide

Conditions
ConditionsYield
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; 3-(S)-(+)-(1-cyano-1,1-diphenylmethyl)pyrrolidine hydrobromide With potassium carbonate In water at 75℃; for 4h;
Stage #2: With hydrogen bromide In water		89.93%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With bis(cyclopentadienyl)titanium dichloride; lithium methanolate In tert-butyl methyl ether for 0.5h;
Stage #2: 2,3-dihydro-5-(2-bromoethyl)benzofuran In tert-butyl methyl ether at 60℃; under 760.051 Torr; for 24h; Inert atmosphere;		89%
Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With bis(cyclopentadienyl)titanium dichloride; lithium methanolate In tert-butyl methyl ether for 0.5h; Inert atmosphere; Glovebox;
Stage #2: 2,3-dihydro-5-(2-bromoethyl)benzofuran In tert-butyl methyl ether at 60℃; for 24h; Sealed tube;		89%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

(2-bromo-2-fluoroethyl)benzene
151588-78-2

(2-bromo-2-fluoroethyl)benzene

C18H19FO

C18H19FO

Conditions
ConditionsYield
With nickel(II) bromide dimethoxyethane; tetra-(n-butyl)ammonium iodide; potassium carbonate; 2,6-bis(4,5-dihydro-1H-imidazol-2-yl)pyridine; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;88%
glutaric anhydride,
108-55-4

glutaric anhydride,

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

C14H18O3

C14H18O3

Conditions
ConditionsYield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0); zinc In N,N-dimethyl acetamide at 80℃; for 12h;87%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide
134002-25-8

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With potassium hydroxide; triethylmethylammonium chloride In water; butanone at 75℃; for 6h; Heating / reflux;
Stage #2: With hydrogen bromide In water; butanone		84.92%
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With potassium carbonate In acetonitrile at 70 - 75℃; for 2h;
Stage #2: With hydrogen bromide In water; acetone at 0 - 25℃; Product distribution / selectivity;
With potassium carbonate In acetonitrile
succinic acid anhydride
108-30-5

succinic acid anhydride

2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

5-(2,3-dihydro-benzofuran-5-yl)-valeric acid

5-(2,3-dihydro-benzofuran-5-yl)-valeric acid

Conditions
ConditionsYield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0); zinc In N,N-dimethyl acetamide at 80℃; for 12h;82%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

3-methyl-2,3,4,6-tetrahydro-1H-benzo[c][2,7]naphthyridin-5-one

3-methyl-2,3,4,6-tetrahydro-1H-benzo[c][2,7]naphthyridin-5-one

C23H24N2O2

C23H24N2O2

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;75%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

1-bromo-3,4,5-trimethoxybenzene
2675-79-8

1-bromo-3,4,5-trimethoxybenzene

A

C19H22O4

C19H22O4

B

C19H22O4

C19H22O4

Conditions
ConditionsYield
With nickel(II) iodide; Bathocuproine; tetrabutylammomium bromide; zinc at 20℃; regioselective reaction;A 75%
B n/a
...Expand
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

Cyclopentyl bromide
137-43-9

Cyclopentyl bromide

C15H19BrO

C15H19BrO

Conditions
ConditionsYield
With nickel(II) iodide; C17H20N2O2; lithium bromide; zinc In 1-methyl-pyrrolidin-2-one at 30℃; for 24h; regioselective reaction;75%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

N-(4-bromophenyl)benzamide
7702-38-7

N-(4-bromophenyl)benzamide

C23H21NO2

C23H21NO2

Conditions
ConditionsYield
With nickel(II) iodide; Bathocuproine; tetrabutylammomium bromide; zinc at 20℃; regioselective reaction;73%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

fenofibrate
49562-28-9

fenofibrate

isopropyl2-(4-(4-(1-(2,3-dihydrobenzofuran-5-yl)ethyl)benzoyl)phenoxy)-2-methylpropanoate

isopropyl2-(4-(4-(1-(2,3-dihydrobenzofuran-5-yl)ethyl)benzoyl)phenoxy)-2-methylpropanoate

Conditions
ConditionsYield
With 2.9-dimethyl-1,10-phenanthroline; nickel(II) perchlorate hexahydrate; tetrabutylammomium bromide In N,N-dimethyl acetamide at 20℃; for 10h; Glovebox; Sealed tube; Electrochemical reaction; Inert atmosphere; regioselective reaction;72%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

5-bromo-2-(4-morpholinyl)pyridine
200064-11-5

5-bromo-2-(4-morpholinyl)pyridine

C19H22N2O2

C19H22N2O2

Conditions
ConditionsYield
With nickel(II) iodide; Bathocuproine; tetrabutylammomium bromide; zinc at 20℃; regioselective reaction;69%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

ethyl 4-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate
1423014-09-8

ethyl 4-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

ethyl 1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-4-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride

ethyl 1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]-4-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride

Conditions
ConditionsYield
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; ethyl 4-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate With potassium carbonate; potassium iodide In acetonitrile Reflux; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether; water Inert atmosphere;		52%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

(3S)-pyrrolidin-3-yl-cyclopentyl(hydroxy)phenyl acetate
719278-77-0

(3S)-pyrrolidin-3-yl-cyclopentyl(hydroxy)phenyl acetate

(3S)-1-[[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrolidin-3-yl]cyclopentyl(hydroxy)phenyl acetate

(3S)-1-[[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrolidin-3-yl]cyclopentyl(hydroxy)phenyl acetate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile for 8h; Heating / reflux;50%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

(3S)-pyrrolidin-3-yl-(2R)-cyclopentyl(hydroxy)phenyl acetate

(3S)-pyrrolidin-3-yl-(2R)-cyclopentyl(hydroxy)phenyl acetate

(3S)-1-[[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrolidin-3-yl](2R)-cyclopentyl(hydroxy)phenyl acetate

(3S)-1-[[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrolidin-3-yl](2R)-cyclopentyl(hydroxy)phenyl acetate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile for 8h; Heating / reflux;46%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

C19H22N2O
910108-52-0

C19H22N2O

2-{(3R)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]piperidin-3-yl}-2,2-diphenylacetamide

2-{(3R)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]piperidin-3-yl}-2,2-diphenylacetamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Heating / reflux;45%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

5-methoxylindole
1006-94-6

5-methoxylindole

C19H19NO2

C19H19NO2

Conditions
ConditionsYield
With norborn-2-ene; palladium diacetate; potassium carbonate at 80℃; for 18h; Inert atmosphere;28%
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide
134002-25-8

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide

darifenacin
133099-04-4

darifenacin

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 2h; Heating / reflux;9%
With potassium phosphate In water; toluene at 20 - 90℃; for 3.5h; Product distribution / selectivity;
With potassium carbonate In water; toluene at 20 - 90℃; for 3.5h; Product distribution / selectivity;
With potassium phosphate In cyclohexane; water at 20 - 90℃; for 3.5h; Product distribution / selectivity;
With potassium hydroxide In acetonitrile at 40 - 50℃; for 18h; Product distribution / selectivity;
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

(S)-darifenacin hydrobromide
133099-07-7

(S)-darifenacin hydrobromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C
2: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / acetonitrile
2: ammonia / methanol / 5 - 7 h / 28 - 45 °C
3: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C
View Scheme
2,3-dihydro-5-(2-bromoethyl)benzofuran
127264-14-6

2,3-dihydro-5-(2-bromoethyl)benzofuran

C21H26N2O

C21H26N2O

2-{(3R)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]piperidin-3-yl}-N,N-dimethyl-2,2-diphenylacetamide

2-{(3R)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]piperidin-3-yl}-N,N-dimethyl-2,2-diphenylacetamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Heating / reflux;

5-(2-Bromoethyl)-2,3-dihydrobenzofuran Chemical Properties

IUPAC Name: 5-(2-Bromoethyl)-2,3-dihydro-1-benzofuran
Synonyms of 5-(2-Bromoethyl)-2,3-dihydrobenzofuram (CAS NO.127264-14-6): 2,3-Dihydro-5-(2-bromoethyl)benzofuran ; 5-(2-Bromo ethyl)-2,3-dihydro benzofuran
CAS NO: 127264-14-6
Molecular Formula: C10H11BrO
Molecular Weight: 227.10
Molecular Structure:
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 2
Polar Surface Area: Å2
Index of Refraction: 1.592
Molar Refractivity: 52.7 cm3
Molar Volume: 155.5 cm3
Surface Tension: 46.7 dyne/cm
Density: 1.459 g/cm3
Flash Point: 113.8 °C
Enthalpy of Vaporization: 50.57 kJ/mol
Boiling Point: 287.7 °C at 760 mmHg
Vapour Pressure: 0.00424 mmHg at 25°C 
Melting Point: 65-67°C 
Appearance: Off-White Powder
SMILES: BrCCc1cc2CCOc2cc1
InChI: InChI=1/C10H11BrO/c11-5-3-8-1-2-10-9(7-8)4-6-12-10/h1-2,7H,3-6H2
InChIKey: JRKZQRRYNCMSCB-UHFFFAOYAA
Std. InChI: InChI=1S/C10H11BrO/c11-5-3-8-1-2-10-9(7-8)4-6-12-10/h1-2,7H,3-6H2
Std. InChIKey: JRKZQRRYNCMSCB-UHFFFAOYSA-N
Product Categories of 5-(2-Bromoethyl)-2,3-dihydrobenzofuram (CAS NO.127264-14-6): Pharmaceutical material and intermeidates;Fluorobenzene;APIs Intermediate;INTERMEDIATESOFDARIFENACIN;Furan&Benzofuran;API intermediates;Aromatics Compounds;Furans;Aromatics;Heterocycles;Benzodiozoles, Benzodioxines & Benzodioxepines;Methyl Halides;Benzofuran

5-(2-Bromoethyl)-2,3-dihydrobenzofuran Safety Profile

 Hazard Codes: IrritantXi

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