o-trifluoromethylbenzyl bromide
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; tris(2,2′-bipyridyl)dichlororuthenium(II) hexahydrate; sodium bromide In water; acetonitrile at 20℃; for 24h; Sealed tube; Inert atmosphere; Irradiation; regioselective reaction; | 62% |
Conditions | Yield |
---|---|
(bromination); | |
With pyridine; phosphorus tribromide at -10 - -5℃; | |
With sulfuric acid; hydrogen bromide | |
With carbon tetrabromide; triphenylphosphine In dichloromethane for 2h; Substitution; reflux; | |
With phosphorus tribromide In dichloromethane; water; toluene |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: (bromination) View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: PBr3, Py / -10 - -5 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: aq. HBr, H2SO4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetra(n-butyl)ammonium hydrogensulfate / ethylene glycol / 4 h / 80 °C / Sealed tube; Inert atmosphere 2: sodium bromide; dipotassium peroxodisulfate; tris(2,2′-bipyridyl)dichlororuthenium(II) hexahydrate / acetonitrile; water / 24 h / 20 °C / Sealed tube; Inert atmosphere; Irradiation View Scheme |
Conditions | Yield |
---|---|
In toluene for 12h; Reflux; | 100% |
In toluene Reflux; | 77% |
In toluene at 80℃; for 16h; |
o-trifluoromethylbenzyl bromide
6-Mercaptopurine
Conditions | Yield |
---|---|
Stage #1: 6-Mercaptopurine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: o-trifluoromethylbenzyl bromide In N,N-dimethyl-formamide at 20℃; Further stages; | A 91% B 99% |
Conditions | Yield |
---|---|
Stage #1: Quinoline-2-thiol With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 0.5h; Stage #2: o-trifluoromethylbenzyl bromide In toluene at 20℃; for 17h; | 99% |
o-trifluoromethylbenzyl bromide
m-nitrobenzene boronic acid
1-(3-nitrobenzyl)-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 50℃; for 16h; | 98% |
o-trifluoromethylbenzyl bromide
5-bromosalicyclaldehyde
5-bromo-2-[2-(trifluoromethyl)benzyloxy]benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 98% |
o-trifluoromethylbenzyl bromide
phenylboronic acid
1-benzyl-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With trans-(imidazole-κN)diiodo(3-isopropylbenzothiazolin-2-ylidene)palladium(II); potassium carbonate In water; N,N-dimethyl-formamide at 60℃; for 2h; Suzuki-Miyaura coupling; | 98% |
Conditions | Yield |
---|---|
Stage #1: methyl 2-cyanoacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.0333333h; Stage #2: o-trifluoromethylbenzyl bromide In dichloromethane at 0 - 20℃; | 98% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; |
ethyl 6-(4-fluorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-4-pyridazinecarboxylate
o-trifluoromethylbenzyl bromide
ethyl 6-(4-fluorophenyl)-5-hydroxy-3-oxo-2-{[2-(trifluoromethyl)phenyl]methyl}-2,3-dihydro-4-pyridazinecarboxylate
Conditions | Yield |
---|---|
Stage #1: ethyl 6-(4-fluorophenyl)-5-hydroxy-3-oxo-2,3-dihydro-4-pyridazinecarboxylate With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.75h; Stage #2: o-trifluoromethylbenzyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; | 97% |
Conditions | Yield |
---|---|
Stage #1: 4-methoxy-2-nitroaniline With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: o-trifluoromethylbenzyl bromide In N,N-dimethyl-formamide at 90℃; Inert atmosphere; | 97% |
o-trifluoromethylbenzyl bromide
N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine
Conditions | Yield |
---|---|
Stage #1: N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: o-trifluoromethylbenzyl bromide In N,N-dimethyl-formamide at 0 - 25℃; for 16h; Inert atmosphere; | 97% |
o-trifluoromethylbenzyl bromide
N-(diphenylmethylene)glycine tert-butyl ester
Conditions | Yield |
---|---|
With C58H42F12N(1+)*Br(1-); potassium hydroxide In water; toluene at -20℃; for 3h; Reagent/catalyst; enantioselective reaction; | 96% |
With C30H32N3O(1+)*Br(1-); potassium hydroxide In water; toluene at -40℃; for 10h; Reagent/catalyst; enantioselective reaction; | 95% |
Conditions | Yield |
---|---|
In toluene; acetonitrile at 20℃; for 1h; Inert atmosphere; | 96% |
o-trifluoromethylbenzyl bromide
demethyltetrandrine
Conditions | Yield |
---|---|
With triethylhexadecylammonium chloride In water at 200℃; for 0.1h; Reagent/catalyst; Solvent; Temperature; | 95.81% |
o-trifluoromethylbenzyl bromide
1-(azidomethyl)-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With sodium azide In water; tert-butyl alcohol | 95.8% |
With sodium azide In water; acetone | 90% |
With sodium azide In water; acetone at 22℃; | 87% |
3,4-dihydro-2(1H)-quinolone
o-trifluoromethylbenzyl bromide
1-[2-(trifluoromethyl)benzyl]-3,4-dihydroquinolin-2(1H)-one
Conditions | Yield |
---|---|
Stage #1: 3,4-dihydro-2(1H)-quinolone With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Stage #2: o-trifluoromethylbenzyl bromide In N,N-dimethyl-formamide at 20℃; | 95% |
(3α,5α)-3-hydroxy-3-(piperazin-1-ylmethyl)androstan-17-one
o-trifluoromethylbenzyl bromide
(3α,5α)-3-hydroxy-3-((4-[2-(trifluoromethyl)benzyl]-piperazin-1-yl)methyl)androstan-17-one
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 95% |
o-trifluoromethylbenzyl bromide
2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isoselenuronium bromide
2-(trifluoromethyl)benzyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-glucopyranoside
Conditions | Yield |
---|---|
With triethylamine at 20℃; | 95% |
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 70℃; for 4h; | 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 24h; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 20℃; for 1h; | 94.5% |
o-trifluoromethylbenzyl bromide
4-methylphenylboronic acid
1-(4-methylbenzyl)-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With trans-(benzimidazole-κN)diiodo(3-isopropylbenzothiazolin-2-ylidene)palladium(II); potassium carbonate In water; N,N-dimethyl-formamide at 60℃; for 17h; Suzuki-Miyaura coupling; | 94% |
o-trifluoromethylbenzyl bromide
N-t-butoxycarbonyl-tyramine
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4h; Williamson Ether Synthesis; Reflux; | 94% |
o-trifluoromethylbenzyl bromide
N-(diphenylmethylene)glycine tert-butyl ester
Conditions | Yield |
---|---|
With C28H28F6N3(1+)*Br(1-); potassium hydroxide In diethyl ether; water at -40℃; for 5h; enantioselective reaction; | 93% |
Conditions | Yield |
---|---|
With sodium carbonate; copper(l) chloride at 100℃; for 24h; Inert atmosphere; Schlenk technique; | 93% |
2-(4-chlorophenoxy)-1,3-propanedioic acid diethyl ester
o-trifluoromethylbenzyl bromide
diethyl 2-(4-chlorophenoxy)-2-[2-(trifluormethyl)benzyl]malonate
Conditions | Yield |
---|---|
Stage #1: 2-(4-chlorophenoxy)-1,3-propanedioic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.333333h; Stage #2: o-trifluoromethylbenzyl bromide In N,N-dimethyl-formamide at 20 - 60℃; | 92% |
1,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-1-pyrrolidnecarboxylate
o-trifluoromethylbenzyl bromide
1,1-dimethylethyl (3S)-3-((3-chloro-4-cyanophenyl){[2-(trifluoromethyl)phenyl]methyl}amino)-1-pyrrolidinecarboxylate
Conditions | Yield |
---|---|
Stage #1: 1,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-1-pyrrolidnecarboxylate With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice; Stage #2: o-trifluoromethylbenzyl bromide In N,N-dimethyl-formamide at 0 - 25℃; for 1h; | 92% |
Stage #1: 1,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-1-pyrrolidnecarboxylate With sodium hydride In hexane; N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: o-trifluoromethylbenzyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #3: With water; ammonium chloride In N,N-dimethyl-formamide | 92% |
Stage #1: 1,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-1-pyrrolidnecarboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil Stage #2: o-trifluoromethylbenzyl bromide In N,N-dimethyl-formamide; mineral oil |
o-trifluoromethylbenzyl bromide
Conditions | Yield |
---|---|
In toluene at 100℃; for 1h; | 92% |
o-trifluoromethylbenzyl bromide
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; | 92% |
o-trifluoromethylbenzyl bromide
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; | 92% |
o-trifluoromethylbenzyl bromide
Conditions | Yield |
---|---|
With triethylamine In acetonitrile for 8h; Reflux; | 91% |
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