40161-55-5

Basic information

• Product Name: 2-Bromo-5-fluorobenzotrifluoride
• Synonyms: 4-FLUORO-2-(TRIFLUOROMETHYL)BROMOBENZENE;2-BROMO-ALPHA,ALPHA,ALPHA,5-TETRAFLUOROTOLUENE;2-BROMO-5-FLUOROBENZOTRIFLUORIDE;1-BROMO-4-FLUORO-2-(TRIFLUOROMETHYL)BENZENE;1-BROMO-2-(TRIFLUOROMETHYL)-4-FLUOROBENZENE;2-Bromo-5-fluorobenzotrifluoride, 97+%;4-Fluoro-2-trifluoromethyl-phenylboronic acid;5-fluoro-2-bromobenzoTrifluoride
• CAS NO: 40161-55-5
• Molecular Formula: C₇H₃BrF₄
• Molecular Weight: 243
• Product Categories: Trifluoromethylbenzene serise;Fluorobenzene;Miscellaneous;Bromine Compounds;Fluorine Compounds;Benzotrifluoride Series;Aryl;C7;Halogenated Hydrocarbons;Aryl Fluorinated Building Blocks;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Halogenated Hydrocarbons;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Fluorine series
• Mol File: 40161-55-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 136-143 °C(lit.)
• Flash Point: 147 °F
• Appearance: /
• Density: 1.695 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.1mmHg at 25°C
• Refractive Index: n20/D 1.465(lit.)
• Storage Temp.: Refrigerator
• BRN: 2643544
• CAS DataBase Reference: 2-Bromo-5-fluorobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-5-fluorobenzotrifluoride(40161-55-5)
• EPA Substance Registry System: 2-Bromo-5-fluorobenzotrifluoride(40161-55-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37/39-37-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 40161-55-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C7H3BrF4/c8-6-2-1-4(9)3-5(6)7(10,11)12/h1-3H

Synthetic route

o-trifluoromethylphenyl bromide (392-83-6) → 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5)

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 (401-80-9) → 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5)

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 (393-36-2) → 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5)

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 (351-36-0) → 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5)

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 (41513-05-7) → 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5)

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 (98-16-8) → 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5)

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 (88-17-5) → 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5)

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 (40161-55-5) + (2R)-methylpiperazine (75336-86-6) → (3R)-1-(4-fluoro-2-(trifluoromethyl)phenyl)-3-methylpiperazine (946399-84-4)

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 (40161-55-5) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(4-fluoro-2-(trifluoromethyl)phenyl)piperazine-1-carboxylate (946399-68-4)

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 (40161-55-5) + isobutyryl chloride (79-30-1) → 1-(4-fluoro-2-(trifluoromethyl)phenyl)-2-methylpropan-1-one

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 (40161-55-5) + acetyl chloride (75-36-5) → 1-(4-fluoro-2-(trifluoromethyl)phenyl)ethan-1-one

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 (40161-55-5) + (E)-tert-butyl 3-(4-((6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (1622308-34-2) → (E)-tert-butyl 3-(4-((2-(4-fluoro-2-(trifluoromethyl)phenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (1622308-62-6)

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 (124-38-9) + 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → 4-fluoro-2-trifluoromethylbenzoic acid (141179-72-8)

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 (40161-55-5) + 4-chloro-phenol (106-48-9) → 1-bromo-4-(4-chlorophenoxy)-2-(trifluoromethyl)benzene (1417782-30-9)

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 (71-23-8) + 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → 1-bromo-4-propoxy-2-(trifluoromethyl)benzene (1186482-11-0)

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 (121-43-7) + 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → (4-fluoro-2-(trifluoromethyl)phenyl)boronic acid

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 (40499-83-0) + 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → 1-[4-fluoro-2-(trifluoromethyl)phenyl]pyrrolidin-3-ol (1198181-18-8)

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 (40161-55-5) + 3-Formylphenylboronic acid (87199-16-4) → C14H8F4O (955930-75-3)

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 (40161-55-5) + bis(pinacol)diborane (73183-34-3) → C13H14BBrF4O2

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 (40161-55-5) + N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide → 4’-fluoro-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-2’-(trifluoromethyl)biphenyl-4-sulfonamide

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 (40161-55-5) → 1-[4'-fluoro-2'-(trifluoromethyl)-1,1'-biphenyl-3-yl]-5-methyl-1H-pyrazole-3-carboxamide

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 (64-18-6) + 1-[4-(2-methylpyrazol-3-yl)phthalazin-1-yl]piperidin-4-amine (1258861-52-7) + 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → [4-fluoro-2-(trifluoromethyl)phenyl]-[1-[4-(2-methylpyrazol-3-yl)phthalazin-1-yl]-4-piperidyl]ammonium formate

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%

N-2-adamantyl-morpholine-2-carboxyamide hydrochloride + 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → N-2-adamantyl-4-(4-fluoro-2-trifluorophenyl)morpholine-2-carboxyamide

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 (652170-12-2) + 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-trifluoromethylphenyl)piperidin-3-ol

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 (40161-55-5) → 2-bromo-5-fluoro-1-nitro-3-trifluoromethyl-benzene (917391-24-3)

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 (542-59-6) + 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → 2-[4-bromo-3-(trifluoromethyl)phenoxy]ethanol (955929-82-5)

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 (1000689-11-1) + 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → (2,3-dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanone (1000689-12-2)

Conditions	Yield
With sodium carbonate In 1,2-dimethoxyethane; water for 14h; Heating / reflux;

2-hydroxyethyl acetate (542-59-6) + 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → C11H10BrF3O3 (955932-76-0)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h;

1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → ({1-[4-fluoro-2-(trifluoromethyl)phenyl]pyrrolidin-3-yl}oxy)acetic acid (1198180-38-9)

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 (40161-55-5) + 4-pyridylboronic acid (1692-15-5) → 4-(4-fluoro-6-trifluoromethylphenyl)pyridine (1214345-41-1)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 85℃; for 10h;

1-bromo-4-fluoro-2-(trifluoromethyl)benzene (40161-55-5) → 4-(4-fluoro-6-trifluoromethylphenyl)pyridine-N-oxide (1219454-46-2)

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 (40161-55-5) → 4-(4-fluoro-6-trifluoromethylphenyl)pyridine-2-carbonitrile (1219454-47-3)

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 (40161-55-5) → 4-(4-fluoro-6-trifluoromethylphenyl)pyridine-2-carboxamide oxime (1219454-48-4)

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

Upstream product

• 401-80-9 3-fluoro-trifluoromethylbenzene 
• 392-83-6 o-trifluoromethylphenyl bromide 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 98-16-8 3-trifluoromethylaniline 
• 393-36-2 4-bromo-3-(trifluoromethyl)aniline 
• 41513-05-7 N-(4-bromo-3-trifluoromethylphenyl)acetamide 
• 351-36-0 N-acetyl-3-trifluoromethylbenzenamine 

Downstream Products

• 1000689-12-2 (2,3-dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanone 
• 1417782-29-6 2-[4-(4-chloro-phenoxy)-2-trifluoromethyl-phenyl]-2-methyl-oxirane 
• 1426802-43-8 C₂₃H₁₈ClF₄NO₃S 
• 1434817-05-6 4-(2,2,2-trifluoroethoxy)-2-trifluoromethylbenzenethiol 
• 1234790-83-0 4-(propyloxy)-2-(trifluoromethyl)benzaldehyde oxime 
• 1268385-32-5 2-{3-[4-(propyloxy)-2-(trifluoromethyl)phenyl]-5-isoxazolyl}-ethanol 
• 1268385-33-6 {3-[4-(propyloxy)-2-(trifluoromethyl)phenyl]-5-isoxazolyl}-acetic Acid 
• 1268385-34-7 methyl {3-[4-(Propyloxy)-2-(trifluoromethyl)phenyl]-5-isoxazolyl}acetate 
• 1268383-41-0 methyl [2-(2,3-difluorophenyl)-5H-imidazo[4,5-d]pyridazin-5-yl]{3-[4-(propyloxy)-2-(trifluoromethyl)phenyl]-5-isoxazolyl}-acetate 
• 1268383-48-7 2-[(2-hydroxyethyl)oxy]ethyl [2-(2,3-difluorophenyl)-5H-imidazo[4,5-d]pyridazin-5-yl]{3-[4-(propyloxy)-2-(trifluoromethyl)phenyl]-5-isoxazolyl}acetate 
• 1234790-81-8 4-(propyloxy)-2-(trifluoromethyl)benzaldehyde 
• 934600-95-0 4-amino-2-trifluoromethylbenzamide 
• 654-70-6 4-amino-2-trifluoromethylbenzonitrile 
• 141179-72-8 4-fluoro-2-trifluoromethylbenzoic acid 

Relevant articles and documents

Synthesis method of 2-bromo-5-fluorobenzotrifluoride

The invention relates to a synthesis method of 2-bromo-5-fluorobenzotrifluoride. The synthesis method comprises the following steps: with benzotrifluoride as a raw material, mixing benzotrifluoride with sulfuric acid, potassium bromide, cuprous bromide and a catalyst, and carrying out a bromination reaction to obtain 2-bromobenzotrifluoride; putting the obtained 2-bromobenzotrifluoride into a DMSOsolvent, adding potassium fluoride and KCoF4, and carrying out a fluorination reaction so as to obtain 2-bromo-5-fluorobenzotrifluoride. According to the method, trifluorotoluene is used as the raw material; the method is a brand-new synthetic route; bromination and fluorination conditions are mild; reaction yield is high; used raw materials are easy to purchase and low in price; and thus, the method has relatively high industrial application value.

A process for preparing 2 - bromo - 5 - fluoro-toluene method

The invention discloses a method for preparing 2-bromine-5-fluorobenzotrifluoride. According to the preparation method, fluorobenzotrifluoride serves as a raw material, under the condition of concentrated sulfuric acid and composite catalysts, bromine is stirred and added dropwise, and 2-bromine-5-fluorobenzotrifluoride is obtained after separation and purification. The yield reaches over 91.1%, the reaction conversion rate is larger than 99%, and selectivity is 92-95%. The raw material applied in the reaction process is convenient to purchase, production cost is low, waste acid obtained in the reaction process can be recycled, post-processing is easy, and the whole technology does not generate a large amount of wastewater containing salt and organic matter. Economic benefits and social benefits are good.

2-bromo-5- fluorine three fluorine methylbenzene preparation method

The invention discloses a method for preparing 2-bromine-5-trifluorotoluene chloride. The method comprises the following step: under an anhydrous condition and in an organic solvent, performing cracking reaction on an anhydrous compound 1 or a compound 1', thereby preparing 2-bromine-5-trifluorotoluene chloride. According to the method, the reaction of an upper amino protecting group of m-trifluoromethyl phenylamine, the bromination reaction and the reaction of removing the amino protecting group can be all performed in one same reaction kettle without transferring or storing materials. The raw materials used in the method disclosed by the invention are cheap and easy to obtain, the reaction step is short, the reaction condition is gentle, the utilization rate of bromine is high, and the positioning selectivity of bromine feeding is high, so that a final product is low in isomeride impurity, high in reaction conversion rate, high in yield, high in product purity, low in production cost is low and applicable to industrialization production. The compound 1 and compound 1' are as shown in the specification.