Conditions | Yield |
---|---|
With hydrogen bromide In benzene at 78℃; for 1h; Bromination; | 100% |
With hydrogen bromide In benzene at 78℃; for 1h; | 100% |
With phosphorus tribromide In diethyl ether at 0℃; for 2h; | 100% |
4-Methoxybenzyl alcohol
A
p-Methoxybenzyl bromide
B
4-methoxy-benzaldehyde
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide In acetic acid for 10h; Ambient temperature; | A 99% B 1% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; dibenzoyl peroxide In Diethyl carbonate for 0.25h; Reflux; Microwave irradiation; | 98% |
With sodium bromate; 2,2'-azobis-(2,4-dimethylvaleronitrile); sulfuric acid; sodium bromide In dichloromethane; water Reflux; | 92% |
With N-Bromosuccinimide; trityl tetrafluoroborate In dichloromethane; benzene at 20℃; Irradiation; Inert atmosphere; chemoselective reaction; | 75% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; dibenzoyl peroxide In various solvent(s) at 90 - 95℃; for 1h; Wohl-Ziegler bromination; | A 95% B 5% |
2-(4-methoxy-benzyloxy)-tetrahydro-pyran
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
With 4-aminophenyl diphenylphosphinite; bromine In dichloromethane at 20℃; for 0.5h; | 95% |
trimethyl(4-methoxybenzyloxy)silane
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
With 4-aminophenyl diphenylphosphinite; bromine In dichloromethane at 20℃; | 95% |
Conditions | Yield |
---|---|
With bromine; trimethylamine borane In chloroform at 0 - 5℃; for 0.0333333h; | 86% |
With chloro-trimethyl-silane; 1,1,3,3-Tetramethyldisiloxane; lithium bromide; zinc(II) chloride In acetonitrile at 80℃; for 0.25h; | 84% |
With Dichloromethylsilane; phosphorus tribromide; iron(III) chloride In acetonitrile for 4h; Heating; | 55% |
ammonium acetate
4-Methoxybenzyl alcohol
A
p-methoxybenzyl acetate
B
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
With N-Bromosuccinimide; triphenylphosphine In acetonitrile at 20℃; for 1.9h; Cooling with ice; | A 86% B 6% |
4-methoxy-1-(methoxymethoxy)methyl benzene
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0916667h; Microwave irradiation; Neat (no solvent); chemoselective reaction; | 81% |
tert-butyl((4-methoxybenzyl)oxy)dimethylsilane
dibromotriphenylphosphorane
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
In dichloromethane for 15h; Ambient temperature; | 80% |
4-methoxy-1-[(ethoxymethoxy)methyl]benzene
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0916667h; Microwave irradiation; Neat (no solvent); chemoselective reaction; | 79% |
butyraldehyde
4-Methoxybenzyl alcohol
A
p-methoxybenzyl butyrate
B
p-Methoxybenzyl bromide
C
4-methoxy-benzaldehyde
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; bromine; sodium hydrogencarbonate In dichloromethane; water | A 50% B 27% C 16% |
4-Methylanisole
A
3-bromo-4-methylanisole
B
2-bromo-4-methylanisole
C
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
With hydrogen bromide; sodium bromide In chloroform; water at 0 - 2℃; Electrolysis; | A 37% B 39% C 12% |
(4-methoxy-benzyl)-trimethyl-silane
A
4-Methylanisole
B
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
With hydrogen bromide; bromine In acetic acid Quantum yield; Product distribution; Ambient temperature; Irradiation; variation of concentration of Br2 and HBr; | A 9.6% B 1% |
tetrachloromethane
N-Bromosuccinimide
4-Methylanisole
dibenzoyl peroxide
p-Methoxybenzyl bromide
bromocyane
N-benzyl-1-(4-methoxyphenyl)-N-methylmethanamine
A
N-benzyl-N-methyl cyanamide
B
p-Methoxybenzyl bromide
bromocyane
N-methyl-N-(4-methyl)benzyl-(4-methoxy)benzylamine
A
methyl-(4-methyl-benzyl)-carbamonitrile
B
p-Methoxybenzyl bromide
4-methoxybenzyl iodide
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
With pyridine; tributyltin bromide at 50℃; Thermodynamic data; Δ G; |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
(4-methoxy-benzyl)-trimethyl-silane
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
With bromine; sodium acetate In acetic acid Irradiation; |
4-Methylanisole
Diethyl 2-bromomalonate
A
p-Methoxybenzyl bromide
B
diethyl malonate
Conditions | Yield |
---|---|
In benzene at 70℃; Product distribution; Mechanism; Irradiation; other substituted toluenes, unsubstituted alkylbenzenes and substituted cumenes; |
Conditions | Yield |
---|---|
With pyridine; tributyltin bromide at 50℃; Thermodynamic data; Δ G; | |
With sodium bromide In N,N-dimethyl-formamide at 25℃; for 2h; Inert atmosphere; | |
With sodium bromide In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; | |
With sodium bromide In N,N-dimethyl-formamide at 25℃; for 2h; Inert atmosphere; |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
hydrogen bromide
4-Methoxybenzyl alcohol
p-Methoxybenzyl bromide
chloroform
bromine
4-Methoxybenzyl alcohol
A
formaldehyd
B
1-bromo-4-methoxy-benzene
C
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 25 °C 1.2: tetrahydrofuran / 20 °C 2.1: NBS; AIBN / CCl4 / Irradiation View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) Na 2: NBS View Scheme |
Conditions | Yield |
---|---|
With hydrogen bromide |
pyridine
p-Methoxybenzyl bromide
N-(4-methoxybenzyl)pyridinium bromide
Conditions | Yield |
---|---|
In acetone; benzene at 20℃; for 24h; | 100% |
In nitrobenzene at 40℃; Rate constant; Mechanism; | |
With ethanol |
p-Methoxybenzyl bromide
triphenylphosphine
((4-methoxyphenyl)methyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In benzene for 24h; Ambient temperature; | 100% |
In toluene at 110℃; | 99% |
In toluene for 10h; Inert atmosphere; Reflux; | 98% |
p-Methoxybenzyl bromide
2',3'-O-isopropylidene-5-fluorouridine
2',3'-O-Isopropylidene-3-(4-methoxybenzyl)-5-fluorouridine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile for 3h; Ambient temperature; | 100% |
With N-ethyl-N,N-diisopropylamine In acetonitrile for 5h; Ambient temperature; Yield given; |
p-Methoxybenzyl bromide
1-(azidomethyl)-4-methoxybenzene
Conditions | Yield |
---|---|
With sodium azide In tetrahydrofuran; water at 80℃; for 3h; Inert atmosphere; | 100% |
With sodium azide; potassium iodide In acetonitrile for 16h; Reflux; Inert atmosphere; | 100% |
With sodium azide In dimethyl sulfoxide at 80℃; | 100% |
p-Methoxybenzyl bromide
triethyl phosphite
diethyl 4-methoxybenzylphosphonate
Conditions | Yield |
---|---|
In water at 80℃; for 5h; Inert atmosphere; | 100% |
Reflux; | 99% |
for 5h; Heating; | 95% |
Conditions | Yield |
---|---|
With water; sodium hydroxide at 20℃; for 0.05h; Microwave irradiation; | 100% |
With dihydrogen peroxide In ethanol for 4h; Reflux; Green chemistry; | 96% |
With pyridine N-oxide for 0.0111111h; Irradiation; with microwave irradiation; | 92% |
homoalylic alcohol
p-Methoxybenzyl bromide
1-(4-methoxybenzyloxy)-3-butene
Conditions | Yield |
---|---|
Stage #1: homoalylic alcohol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: p-Methoxybenzyl bromide In tetrahydrofuran at 0℃; for 1h; | 100% |
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: p-Methoxybenzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 0 - 20℃; for 17h; Inert atmosphere; | 100% |
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h; | 96% |
(4S)-4-((2R)-2-hydroxypent-4-enyl)-2,2-dimethyl-1,3-dioxolane
p-Methoxybenzyl bromide
(S)-4-[(R)-2-(4-Methoxy-benzyloxy)-pent-4-enyl]-2,2-dimethyl-[1,3]dioxolane
Conditions | Yield |
---|---|
Stage #1: (4S)-4-((2R)-2-hydroxypent-4-enyl)-2,2-dimethyl-1,3-dioxolane With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: p-Methoxybenzyl bromide In N,N-dimethyl-formamide at 20℃; | 100% |
Stage #1: (4S)-4-((2R)-2-hydroxypent-4-enyl)-2,2-dimethyl-1,3-dioxolane With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: p-Methoxybenzyl bromide In N,N-dimethyl-formamide at 20℃; Further stages.; | 100% |
p-Methoxybenzyl bromide
1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole
Conditions | Yield |
---|---|
In ethyl acetate at 20℃; for 2h; | 100% |
tetrahydropyran-2-yl 4,6-O-(4-methoxyphenyl)methylidene-5-deoxy-5-thio-α-D-glucopyranoside
p-Methoxybenzyl bromide
tetrahydropyran-2-yl 2,3-di-O-(4-methoxyphenyl)methyl-4,6-O-(4-methoxyphenyl)methylidene-5-deoxy-5-thio-α-D-glucopyranoside
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide; toluene at 20℃; for 2h; | 100% |
p-Methoxybenzyl bromide
2-amino-1-hydroxy-indole-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; | 100% |
(S)-3,7-dimethyl-6-octen-1-ol
p-Methoxybenzyl bromide
(S)-4-methoxybenzyl 3,7-dimethyl-6-octenyl ether
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 48h; Heating; | 100% |
p-Methoxybenzyl bromide
coumarin 2
7-[ethyl-(4-methoxy-benzyl)amino]-4,6-dimethyl-chromen-2-one
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide Heating; | 100% |
p-Methoxybenzyl bromide
1-butyl-4,5-bis(4-chlorophenyl)-3-(4-methoxybenzyl)-4-(methoxycarbonyl)-4,5-dihydro-1H-imidazolium iodide
Conditions | Yield |
---|---|
With sodium iodide In acetone at 20℃; for 18h; | 100% |
2,3-bis(methoxycarbonyl)phenol
p-Methoxybenzyl bromide
3-(4-methoxy-benzyloxy)-phthalic acid dimethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 6h; Heating / reflux; | 100% |
p-Methoxybenzyl bromide
ethyl 3-trifluoromethyl-1H-pyrazole-4-carboxylate
ethyl 1-[(4-methoxyphenyl)methyl]-3-(trifluoromethyl)pyrazole-4-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h; | 100% |
(1R)-N-[(2-benzyloxy)-1-(hydroxymethyl)ethyl]chloromethane sulphonamide
p-Methoxybenzyl bromide
C19H24ClNO5S
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With sodium iodide In acetone at 20℃; for 18h; | 100% |
4-cyanobenzenethiol
p-Methoxybenzyl bromide
4-[(4-methoxybenzyl)thio]benzonitrile
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 18h; | 100% |
2-iodo-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)benzamide
p-Methoxybenzyl bromide
C24H18F6INO3
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide | 100% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 0 - 24℃; | 100% |
N-(tert-butoxycarbonyl)-D-tyrosine
p-Methoxybenzyl bromide
4-methoxybenzyl N-(tert-butoxycarbonyl)-D-tyrosinate
Conditions | Yield |
---|---|
Stage #1: N-(tert-butoxycarbonyl)-D-tyrosine With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; Stage #2: p-Methoxybenzyl bromide In N,N-dimethyl-formamide at 20℃; Stage #3: With acetic acid In water; ethyl acetate; N,N-dimethyl-formamide pH=5; | 100% |
Stage #1: N-(tert-butoxycarbonyl)-D-tyrosine With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; Stage #2: p-Methoxybenzyl bromide In N,N-dimethyl-formamide at 20℃; | 100% |
2-bromo-6-methylbenzoic acid (S)-1-[(R)-1-hydroxyallyl]hexyl ester
p-Methoxybenzyl bromide
(-)-2-bromo-6-methylbenzoic acid (S)-1-[(R)-1-(4-methoxybenzyloxy)allyl]hexyl ester
Conditions | Yield |
---|---|
With potassium hexamethylsilazane; triethylamine In tetrahydrofuran; toluene at -78 - 20℃; for 1.5h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 50℃; | 100% |
With caesium carbonate In acetonitrile at 50℃; Inert atmosphere; | 100% |
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone at 55℃; | 65.6% |
Conditions | Yield |
---|---|
In ethyl acetate at 0 - 20℃; for 0.333333h; | 100% |
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
Stage #1: (2R,3R,4S,5S,6S)-4,5-dibenzyloxy-2-[(tert-butyl(dimethyl)silyl)oxymethyl]-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]tetrahydropyran-3-ol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: p-Methoxybenzyl bromide In tetrahydrofuran at 0 - 20℃; for 3h; | 100% |
p-Methoxybenzyl bromide
(piperidin-4-yl)carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 1h; | 81% |
With triethylamine In ethanol |
benzhydrylidene aza-glycinyl-D-phenylalanine tert-butyl ester
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
Stage #1: benzhydrylidene aza-glycinyl-D-phenylalanine tert-butyl ester With tetraethylammonium hydroxide In tetrahydrofuran; water at 20℃; for 0.5h; Inert atmosphere; Stage #2: p-Methoxybenzyl bromide In tetrahydrofuran; water at 20℃; Inert atmosphere; | 100% |
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