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inquiryName: 1-Bromo-4-fluoro-2-(trifluoromethyl)benzene Synonyms: 2-bromo-5-fluorobenzotrifluoride CAS:40161-55-5 MF: C7H3BrF4 Appearance: colorless transparent liquid Storage: Preserve in well-closed, light-resistant and airtight containers. Pack
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inquiry2-Bromo-5-fluorobenzotrifluoride Basic information Product Name: 2-Bromo-5-fluorobenzotrifluoride Synonyms: 4-FLUORO-2-(TRIFLUOROMETHYL)BROMOBENZ
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inquiryo-trifluoromethylphenyl bromide
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With potassium fluoride; potassium tetrafluorocobaltate In dimethyl sulfoxide for 5h; Reflux; | 96.7% |
Multi-step reaction with 3 steps 1.1: nitric acid; sulfuric acid / 50 - 60 °C 2.1: piperazine; hydrogen / methanol / 80 - 90 °C / 6000.6 - 7500.75 Torr 3.1: hydrogen fluoride; potassium fluoride; sodium nitrite / 0.5 h / -10 - 5 °C 3.2: 60 °C View Scheme |
3-fluoro-trifluoromethylbenzene
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With ferric(III) bromide; sulfuric acid; tetrabutylammomium bromide; bromine; lithium bromide at 20 - 25℃; for 8h; Temperature; | 93.09% |
With N-Bromosuccinimide; sulfuric acid; tetrabutylammomium bromide; bromine; ammonium bromide at 20℃; under 760.051 Torr; | 92.3% |
4-bromo-3-(trifluoromethyl)aniline
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
Stage #1: 4-bromo-3-(trifluoromethyl)aniline With potassium fluoride; hydrogen fluoride; sodium nitrite at -10 - 5℃; for 0.5h; Stage #2: at 60℃; | 86.8% |
Stage #1: 4-bromo-3-(trifluoromethyl)aniline With hydrogenchloride In water at 25℃; for 3h; Stage #2: With sodium nitrite In water at 0℃; Concentration; Reagent/catalyst; Solvent; Temperature; Further stages; | 82% |
With hydrogen fluoride; sodium nitrite at -10 - 125℃; for 1.5h; Autoclave; | 80% |
N-acetyl-3-trifluoromethylbenzenamine
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid; hydrogen bromide; dihydrogen peroxide / 0.5 h / 25 °C / Inert atmosphere 2: hydrogenchloride / water / 90 °C 3: sodium nitrite; hydrogen fluoride / 1.5 h / -10 - 125 °C / Autoclave View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium chlorate; acetic acid; iron; bromine / water / 11 h / 65 °C 2.1: sodium hydroxide / methanol / 5 h / 90 °C 3.1: hydrogenchloride / water / 3 h / 25 °C 3.2: 0 °C View Scheme |
N-(4-bromo-3-trifluoromethylphenyl)acetamide
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 90 °C 2: sodium nitrite; hydrogen fluoride / 1.5 h / -10 - 125 °C / Autoclave View Scheme |
3-trifluoromethylaniline
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 1 h / 60 °C 2.1: sodium chlorate; acetic acid; iron; bromine / water / 11 h / 65 °C 3.1: sodium hydroxide / methanol / 5 h / 90 °C 4.1: hydrogenchloride / water / 3 h / 25 °C 4.2: 0 °C View Scheme |
2-(trifluoromethyl)benzenamine
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydrogen bromide; sodium nitrite / water / 0.33 h / 0 - 5 °C 1.2: 0.33 h / 20 °C 2.1: nitric acid; sulfuric acid / 50 - 60 °C 3.1: piperazine; hydrogen / methanol / 80 - 90 °C / 6000.6 - 7500.75 Torr 4.1: hydrogen fluoride; potassium fluoride; sodium nitrite / 0.5 h / -10 - 5 °C 4.2: 60 °C View Scheme |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
(2R)-methylpiperazine
(3R)-1-(4-fluoro-2-(trifluoromethyl)phenyl)-3-methylpiperazine
Conditions | Yield |
---|---|
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene Buchwald amination; regioselective reaction; | 100% |
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 5h; Inert atmosphere; | 99% |
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 105℃; for 3.5h; Inert atmosphere; | 98% |
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 5h; Buchwald amination; | 73% |
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100 - 110℃; for 3 - 5h; Product distribution / selectivity; | 33.6% |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
1-t-Butoxycarbonylpiperazine
tert-butyl 4-(4-fluoro-2-(trifluoromethyl)phenyl)piperazine-1-carboxylate
Conditions | Yield |
---|---|
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 0.5h; Microwave irradiation; | 100% |
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; for 0.5h; Buchwald amination; Microwave irradiation; | 100% |
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 16h; Inert atmosphere; | 83% |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
isobutyryl chloride
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-fluoro-2-(trifluoromethyl)benzene With isopropylmagnesium chloride In tetrahydrofuran; tert-butyl methyl ether at 20℃; for 1.5h; Inert atmosphere; Stage #2: isobutyryl chloride In tert-butyl methyl ether at 20℃; for 3h; Inert atmosphere; | 97.6% |
Stage #1: 1-bromo-4-fluoro-2-(trifluoromethyl)benzene With isopropylmagnesium chloride In tetrahydrofuran; toluene at 25 - 30℃; for 1h; Large scale; Stage #2: isobutyryl chloride With copper(l) chloride In tetrahydrofuran; toluene at 25 - 40℃; for 1.5h; Temperature; Large scale; |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
acetyl chloride
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-fluoro-2-(trifluoromethyl)benzene With isopropylmagnesium chloride In tetrahydrofuran; tert-butyl methyl ether at 25 - 30℃; for 0.5h; Large scale; Stage #2: acetyl chloride With copper(l) chloride In tetrahydrofuran; tert-butyl methyl ether at 38 - 42℃; for 1h; Solvent; Temperature; Reagent/catalyst; Large scale; | 96.4% |
Stage #1: 1-bromo-4-fluoro-2-(trifluoromethyl)benzene With isopropyl chloride; magnesium; isopropyl bromide In tetrahydrofuran; toluene at 20 - 60℃; Stage #2: acetyl chloride With copper(l) chloride In tetrahydrofuran; toluene at -5℃; for 2h; Temperature; |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
(E)-tert-butyl 3-(4-((6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate
(E)-tert-butyl 3-(4-((2-(4-fluoro-2-(trifluoromethyl)phenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate
Conditions | Yield |
---|---|
With chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 150℃; for 2h; Microwave irradiation; Sealed tube; Inert atmosphere; | 94% |
carbon dioxide
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
4-fluoro-2-trifluoromethylbenzoic acid
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-fluoro-2-(trifluoromethyl)benzene With iodine; magnesium In tetrahydrofuran at 50℃; for 1h; Inert atmosphere; Cooling; Stage #2: carbon dioxide In tetrahydrofuran at 5 - 25℃; for 2h; Solvent; Temperature; Inert atmosphere; | 90% |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
4-chloro-phenol
1-bromo-4-(4-chlorophenoxy)-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
Stage #1: 4-chloro-phenol With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 120℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-4-fluoro-2-(trifluoromethyl)benzene In 1-methyl-pyrrolidin-2-one at 140℃; for 5h; Inert atmosphere; | 87.99% |
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 5h; | 3.14 g |
propan-1-ol
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
1-bromo-4-propoxy-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With sodium hydride In mineral oil at 20 - 145℃; Microwave irradiation; Sealed tube; | 86% |
Stage #1: propan-1-ol With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium tert-butylate In toluene at 50℃; for 0.5h; Inert atmosphere; Stage #2: 1-bromo-4-fluoro-2-(trifluoromethyl)benzene In toluene at 50℃; for 0.5h; Inert atmosphere; |
Trimethyl borate
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-fluoro-2-(trifluoromethyl)benzene With n-butyllithium In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor; | 85% |
pyrrolidin-3-ol
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
1-[4-fluoro-2-(trifluoromethyl)phenyl]pyrrolidin-3-ol
Conditions | Yield |
---|---|
With caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 85℃; for 16h; Inert atmosphere; | 84% |
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene at 85℃; for 16h; Inert atmosphere; | 84% |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
3-Formylphenylboronic acid
C14H8F4O
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80℃; for 5h; Inert atmosphere; | 77% |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
bis(pinacol)diborane
Conditions | Yield |
---|---|
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Glovebox; | 71% |
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Glovebox; | 71% |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium; sodium carbonate In 1,4-dioxane; water at 110℃; for 6h; Inert atmosphere; | 47% |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
Stage #1: 1-(3-bromophenyl)-5-methyl-1H-pyrazole-3-carboxamide With 4,4,5,5-tetramethyl-2-(3,3,4,4-tetramethylborolan-1-yl)-1,3,2-dioxaborolane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide at 140℃; for 0.333333h; Microwave irradiation; Stage #2: 1-bromo-4-fluoro-2-(trifluoromethyl)benzene With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; dimethyl sulfoxide at 140℃; for 0.777778h; Microwave irradiation; | 41% |
formic acid
1-[4-(2-methylpyrazol-3-yl)phthalazin-1-yl]piperidin-4-amine
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
Stage #1: 1-[4-(2-methylpyrazol-3-yl)phthalazin-1-yl]piperidin-4-amine; 1-bromo-4-fluoro-2-(trifluoromethyl)benzene With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 110℃; Inert atmosphere; Stage #2: formic acid In acetonitrile | 13% |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 5h; | 10% |
4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochloride
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 4h; |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
2-bromo-5-fluoro-1-nitro-3-trifluoromethyl-benzene
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-fluoro-2-(trifluoromethyl)benzene With sulfuric acid; sulfur trioxide; potassium nitrate In dichloromethane at 20 - 30℃; for 25h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water |
2-hydroxyethyl acetate
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
2-[4-bromo-3-(trifluoromethyl)phenoxy]ethanol
Conditions | Yield |
---|---|
Stage #1: 2-hydroxyethyl acetate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 1-bromo-4-fluoro-2-(trifluoromethyl)benzene In N,N-dimethyl-formamide at 20℃; for 1.5h; |
(2,3-dihydrobenzo[1,4]oxazin-4-yl)[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,5-dihydropyrrol-1-yl]methanone
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
(2,3-dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanone
Conditions | Yield |
---|---|
With sodium carbonate In 1,2-dimethoxyethane; water for 14h; Heating / reflux; |
2-hydroxyethyl acetate
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
C11H10BrF3O3
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
({1-[4-fluoro-2-(trifluoromethyl)phenyl]pyrrolidin-3-yl}oxy)acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / 85 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 60 °C 2.2: 1 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / toluene / 16 h / 85 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; oil / 0.5 h / 60 °C 2.2: 1 h / 60 °C View Scheme |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
4-pyridylboronic acid
4-(4-fluoro-6-trifluoromethylphenyl)pyridine
Conditions | Yield |
---|---|
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 85℃; for 10h; |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
4-(4-fluoro-6-trifluoromethylphenyl)pyridine-N-oxide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 10 h / 85 °C 2: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 0 °C View Scheme |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
4-(4-fluoro-6-trifluoromethylphenyl)pyridine-2-carbonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 10 h / 85 °C 2: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 0 °C 3: triethylamine / acetonitrile / 14 h / 90 °C View Scheme |
1-bromo-4-fluoro-2-(trifluoromethyl)benzene
4-(4-fluoro-6-trifluoromethylphenyl)pyridine-2-carboxamide oxime
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 10 h / 85 °C 2: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 0 °C 3: triethylamine / acetonitrile / 14 h / 90 °C 4: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 3 h / 20 °C View Scheme |
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