108-37-2

Basic information

• Product Name: 1 -Bromo-3-chloro benzene
• Synonyms: 1-Bromo-3-chlorobenzene;1-Chloro-3-bromobenzene;3-Bromo-1-chlorobenzene;3-Bromophenyl chloride;3-Chloro-1-bromobenzene;3-Chlorobromobenzene;3-Chlorophenyl bromide;NSC 53548;m-Bromochlorobenzene;m-Bromophenyl chloride;m-Chlorobromobenzene
• CAS NO: 108-37-2
• Molecular Formula: C₆H₄BrCl
• Molecular Weight: 191.45
• EINECS: 203-575-8
• Mol File: 108-37-2.mol
• Article Data: 27

Chemical Properties

• Melting Point: -21.5℃
• Boiling Point: 194.7 °C at 760 mmHg
• Flash Point: 80.6 °C
• Appearance: Clear colourless to light yellow liquid
• Density: 1.628 g/cm³
• Vapor Pressure: 0.609mmHg at 25°C
• Refractive Index: 1.574
• Water Solubility: Insoluble
• CAS DataBase Reference: 1 -Bromo-3-chloro benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1 -Bromo-3-chloro benzene(108-37-2)
• EPA Substance Registry System: 1 -Bromo-3-chloro benzene(108-37-2)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R20/22:; R36/37/38:
• Safety Statements: S26:; S37/39:
• Hazardous Substances Data: 108-37-2(Hazardous Substances Data)

Usage

General Description

1-Bromo-3-chlorobenzene, alternatively known as m-Bromochlorobenzene, is a halogenated aromatic organic compound. It consists of a benzene ring substituted with one bromine atom and one chlorine atom. It is often utilized as an intermediate in the synthesis of other organic compounds. The compound is colourless to light yellow with a slightly sweet smell and has the molecular formula C6H4BrCl. It is relatively stable but should be kept away from strong oxidising agents and heat, as it could decompose and produce toxic fumes including hydrogen chloride and bromide. Appropriate care should be taken while handling this chemical due to its potential to cause skin, eye, and respiratory irritation.

InChI:InChI=1/C6H4BrCl/c7-5-2-1-3-6(8)4-5/h1-4H

Synthetic route

3-chlorobenzenediazonium tetrafluoroborate (456-39-3) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With dibenzo-18-crown-6; potassium bromide; copper(ll) bromide; 1,10-Phenanthroline; copper(I) bromide In acetonitrile at 20℃; for 0.333333h; Sandmeyer bromination;	99%

4-bromo-2-chloroiodobenzene (31928-47-9) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With [Ir(2-phenylpyridine)-2-(4,4’-di-tert-butyl-2,2’-bipyridine)]PF6; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 1.5h; Irradiation;	92%

(3-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate (1416277-01-4) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With copper(I) bromide In acetonitrile at 80℃; for 2h;	92%

3-bromo-benzenediazonium; tetrachloro cuprate(II) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
In dimethyl sulfoxide Ambient temperature;	90%

m-chlorophenylhydrazine hydrochloride (2312-23-4) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With boron tribromide; dimethyl sulfoxide at 80℃; for 1h;	90%

C6H4ClN2(1+)*C6H4NO4S2(1-) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution;	75%
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution;	71%

3-bromobenzenediazonium o-benzenedisulfonimide → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 20℃; Substitution;	74%

3-chlorophenylboronic acid (63503-60-6) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 81℃; for 8h;	59%

chlorobenzene (108-90-7) → bromochlorobenzene (106-39-8) + 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With bromine trifluoride; bromine at 0 - 10℃;	A 25% B 5%

2-(3-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (635305-47-4) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With copper(ll) bromide In methanol Heating;	24%

4-Bromo-2-chloro-benzoic Acid (59748-90-2) + 5-bromo-3-chloro-3',5'-dimethyl-[1,1'-biphenyl]-2-carboxylic acid (1344681-59-9) → 1-bromo-3-chlorobenzene (108-37-2) + 3-bromo-5-chloro-3',5'-dimethyl-1,1'-biphenyl (1344681-53-3)

Conditions	Yield
With silver carbonate In dimethyl sulfoxide at 120℃; for 4h;	A 18% B 5%

bromobenzene (108-86-1) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With thallium chloride at 100℃; durch Chlorieren;

3-chlorobenzenediazonium (17333-84-5) → 1-bromo-3-chlorobenzene (108-37-2)

3-Bromonitrobenzene (585-79-5) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With tetrachloromethane at 270℃;

3-chloro-aniline (108-42-9) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With hydrogen bromide; acetic acid at 5 - 10℃; Einleiten von N2O3 und anschliessendes Erhitzen;
Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuBr und HBr;
Stage #1: 3-chloro-aniline With hydrogen bromide; sodium nitrite In water at 0 - 5℃; Stage #2: With hydrogen bromide; copper(I) bromide In water

Acetanilid (103-84-4) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
durch sukzessive Chlorierung, Bromierung, Verseifung und Behandlung mit Aethylnitrit;

3-bromoaniline (591-19-5) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuCl;

1-bromo-2,3-dichlorobenzene (56961-77-4) → 1-bromo-3-chlorobenzene (108-37-2) + 1,2-dichloro-benzene (95-50-1)

Conditions	Yield
With hexane at 25℃; for 4h; Irradiation; relative rate of dehalogenation, other polyhalobenzenes;

4-chloro-2-bromoaniline (873-38-1) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With tetrafluoroboric acid; N,N-dimethyl-formamide; sodium nitrite 1) water, 0 deg C, 2 h, 2) 40 deg C, 30 min; Yield given. Multistep reaction;

1,3-Dichlorobenzene (541-73-1) → 1-bromo-3-chlorobenzene (108-37-2) + 1,3-dibromobenzene (108-36-1)

Conditions	Yield
With bromobenzene; Cu-HZSM-5 zeolite at 399.9℃; Mechanism; Product distribution;	A 11.6 % Chromat. B 3.2 % Chromat.

1,3-dibromo-5-chlorobenzene (14862-52-3) + benzene (71-43-2) → 1-bromo-3-chlorobenzene (108-37-2) + m-chlorobiphenyl (2051-61-8) + 3-bromo-5-chloro-1,1’-biphenyl (126866-35-1) + 5′-chloro-1,1′:3′,1″-terphenyl

Conditions	Yield
at 25℃; for 20h;	A 1.0 % Chromat. B 30.3 % Chromat. C 25.2 % Chromat. D 36.1 % Chromat.

1,4-dibromo-2-chlorobenzene (3460-24-0) + benzene (71-43-2) → 1-bromo-3-chlorobenzene (108-37-2) + 4-bromo-1,1'-biphenyl (92-66-0) + 4-bromo-3-chloro-1,1'-biphenyl (91354-08-4) + 2-chloro-4-bromobiphenyl (58775-86-3)

Conditions	Yield
at 25℃; for 20h;	A 2.7 % Chromat. B 8.2 % Chromat. C 4.3 % Chromat. D 17.1 % Chromat.

3-chloro-benzenecarboperoxoic acid (937-14-4) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With Bromotrichloromethane; cyclohexane In 1,2-dichloro-ethane at 65℃; for 24h; Product distribution; Mechanism;

bromine (7726-95-6) + chlorobenzene (108-90-7) → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
at 475℃;

3-chloro-phenyl-mercury acetate → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With bromine; acetic acid

diazotized m-chloro-aniline → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With hydrogen bromide Behandlung mit CuBr;

m-bromo-benzenediazonium chloroplatinate → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With sodium carbonate

silver-<3-chloro benzoate> → 1-bromo-3-chlorobenzene (108-37-2)

Conditions	Yield
With tetrachloromethane; bromine

chlorobenzene (108-90-7) → 1-bromo-3-chlorobenzene (108-37-2) + 2-chloro-1-bromo-benzene; 4-chloro-1-bromo-benzene

Conditions	Yield
With bromine at 475℃;

1-bromo-3-chlorobenzene (108-37-2) + carbon dioxide (124-38-9) → 2-bromo-6-chlorobenzoic acid (93224-85-2)

Conditions	Yield
Stage #1: 1-bromo-3-chlorobenzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: carbon dioxide In tetrahydrofuran at -78 - 20℃; for 2h;	100%
With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -75℃; for 2h;	94%
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78℃; for 2h; Stage #2: carbon dioxide In tetrahydrofuran; hexanes for 0.25h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexanes; water Product distribution / selectivity;	85%
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78℃; for 0.333333h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -75℃; for 4h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at -70 - 20℃; for 5.5h; Inert atmosphere;

1-bromo-3-chlorobenzene (108-37-2) + acrylic acid n-butyl ester (141-32-2) → 3-chloro-trans-cinnamic acid n-butyl ester (131061-13-7)

Conditions	Yield
With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride In N,N-dimethyl acetamide at 120℃; for 5h; Heck reaction;	100%
With tetrabutylammonium acetate; palladium diacetate at 100℃; for 0.5h; Heck reaction; Air atmosphere; Ionic liquid; chemoselective reaction;

1-bromo-3-chlorobenzene (108-37-2) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(3-chlorophenyl)piperazine-1-carboxylate (186790-11-4)

Conditions	Yield
Stage #1: 1-bromo-3-chlorobenzene; 1-t-Butoxycarbonylpiperazine With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In xylene at 50℃; Stage #2: With macroporous polymer-supported isocyanate In xylene at 50℃; for 24h;	100%
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃;	83%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos In 1,4-dioxane at 95℃; for 2h; Inert atmosphere;	61.2%
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; DavePhos
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 16h; Inert atmosphere; Heating;	1.5 g

1-bromo-3-chlorobenzene (108-37-2) → 3-monochlorophenol (108-43-0)

Conditions	Yield
With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1h;	99%
Multi-step reaction with 2 steps 1: copper dichloride; potassium carbonate / 20 h / 130 °C / Inert atmosphere; Schlenk technique 2: potassium hydroxide / dimethyl sulfoxide / 3 h / 100 °C / Schlenk technique View Scheme
Multi-step reaction with 2 steps 1: fac-tris(2-phenylpyridinato-N,C2')iridium(III); tributyl-amine; water / acetonitrile / 36 h / 25 °C / Schlenk technique; Inert atmosphere; Sealed tube; Irradiation 2: air / 16 h / 25 °C / Inert atmosphere View Scheme
With copper(l) iodide; C20H20N4O4; caesium carbonate; Benzaldoxime In dimethyl sulfoxide at 80℃; for 18h; Inert atmosphere; Glovebox;

1-bromo-3-chlorobenzene (108-37-2) + Methyl formate (107-31-3) → 1-chloro-3-methoxy-benzene (2845-89-8)

Conditions	Yield
With copper(I) bromide In methanol; sodium methylate	99%

1-bromo-3-chlorobenzene (108-37-2) + di-tert-butyl dicarbonate (24424-99-5) → 3-chlorobenzoic acid tert-butyl ester (16537-17-0)

Conditions	Yield
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -10℃; Stage #3: With citric acid In tetrahydrofuran; hexane; toluene Further stages.;	99%
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃; for 1h; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -10℃; for 2h; Inert atmosphere;	99%
Stage #1: 1-bromo-3-chlorobenzene With n-hexyllithium In 2-methyltetrahydrofuran; hexane at 0℃; for 0.000194444h; Flow reactor; Stage #2: di-tert-butyl dicarbonate In 2-methyltetrahydrofuran; hexane at 0℃; for 0.00475h; Flow reactor;	50%

1-bromo-3-chlorobenzene (108-37-2) + carbon monoxide (201230-82-2) + aniline (62-53-3) → 3-chloro-N-phenylbenzamide (6832-92-4)

Conditions	Yield
With palladium diacetate; sodium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 80℃; under 760.051 Torr; for 15h;	99%

1-bromo-3-chlorobenzene (108-37-2) + C17H16N4O (1358787-39-9) → C23H19ClN4O (1358787-91-3)

Conditions	Yield
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃;	99%

1-bromo-3-chlorobenzene (108-37-2) + carbon monoxide (201230-82-2) + benzylamine (100-46-9) → N-benzyl-(3-chloro)benzamide (82082-49-3)

Conditions	Yield
With triethylamine In toluene at 70℃; under 760.051 Torr; for 7h; Catalytic behavior;	99%

1-bromo-3-chlorobenzene (108-37-2) + 9H-carbazole (86-74-8) → 9-(3-chlorophenyl)-9H-carbazole (19222-81-2)

Conditions	Yield
Stage #1: 9H-carbazole With methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: 1-bromo-3-chlorobenzene With PdCl(π-allyl)(cyclohexyl-(1-methyl-2,2-diphenylcyclopropylphophine)) In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 108 - 112℃; for 2h; Inert atmosphere;	99%
Stage #1: 9H-carbazole With methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5 - 20℃; for 0.333333h; Inert atmosphere; Stage #2: 1-bromo-3-chlorobenzene With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 110℃; for 1h;	98.5%
With bis(di-tert-butyl(2-butenyl)phosphine)dichloropalladium; sodium t-butanolate In o-xylene at 135℃; for 9h; Reagent/catalyst; Inert atmosphere;	95%

1-bromo-3-chlorobenzene (108-37-2) → chlorobenzene (108-90-7) + benzene (71-43-2)

Conditions	Yield
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 4h; ultrasonic acceleration of reduction;	A 98% B n/a

1-bromo-3-chlorobenzene (108-37-2) + phenylboronic acid (98-80-6) → m-chlorobiphenyl (2051-61-8)

Conditions	Yield
With 3,5-di-tert-butyl-2-hydroxybenzaldehyde; potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 2h; Suzuki-Miyaura Coupling;	98%
With (BeDABCO)2Pd2Cl6; potassium carbonate In ethanol at 20℃; for 0.0166667h; Suzuki-Miyaura Coupling;	97%
With potassium phosphate; tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine; palladium dichloride In o-xylene at 90℃; for 2h; Concentration; Time; Temperature; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	97%

1-bromo-3-chlorobenzene (108-37-2) + methylamine (74-89-5) → 3-chloro-N-methylaniline (7006-52-2)

Conditions	Yield
With copper In water at 100℃; for 12h; Ullmann reaction;	98%

1-bromo-3-chlorobenzene (108-37-2) + tributylphenylstannane (960-16-7) → m-chlorobiphenyl (2051-61-8)

Conditions	Yield
With 2C13H19N2(1+)*Cl6Pd2(2+); cesium fluoride In N,N-dimethyl-formamide at 120℃; for 0.0166667h; Stille Cross Coupling; Microwave irradiation;	98%
With [Pd{C6H2-(CH2CH2NH2)-(OMe)2-3,4}Br(PPh3)]; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.0333333h; Stille coupling; Microwave irradiation; chemoselective reaction;	92%
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 0.0666667h; Stille coupling; Microwave irradiation; chemoselective reaction;	90%
With dmap; palladium dichloride for 0.333333h; Stille Cross Coupling; Microwave irradiation;	61%

1H-imidazole (288-32-4) + 1-bromo-3-chlorobenzene (108-37-2) → 1-(3-chlorophenyl)-1H-imidazole (51581-52-3)

Conditions	Yield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 48h; Inert atmosphere;	98%

1-bromo-3-chlorobenzene (108-37-2) + 1,1,1,3,5,5,5-heptamethyltrisiloxan (1873-88-7) → 3-(3-bromo-5-chlorophenyl)-1,1,1,3,5,5,5-heptamethyltrisiloxane

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 2.9-dimethyl-1,10-phenanthroline In 1,4-dioxane at 100℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; regioselective reaction;	98%

styrene (292638-84-7) + 1-bromo-3-chlorobenzene (108-37-2) + benzonitrile (100-47-0) → 6-chloro-2,4-diphenylquinoline (21923-40-0)

Conditions	Yield
With N-n-butyl-N-methylpiperidine bis(trifluoromethanesulfonyl)imide salt; acetylferrocene; H2SiEt2 at 60℃; for 8h; Reagent/catalyst;	97.9%

1-bromo-3-chlorobenzene (108-37-2) + ethyl trifluoroacetate, (383-63-1) → 1-(3-chlorophenyl)-2,2,2-trifluoroethanone (321-31-3)

Conditions	Yield
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium In tetrahydrofuran at -78 - -50℃; for 1h; Stage #2: ethyl trifluoroacetate, In tetrahydrofuran at -78 - 20℃; Reagent/catalyst; Solvent; Temperature;	97.3%
Stage #1: 1-bromo-3-chlorobenzene With magnesium In diethyl ether Inert atmosphere; Stage #2: ethyl trifluoroacetate, In diethyl ether at -78 - -50℃; for 3.5h; Inert atmosphere;

methanol (67-56-1) + 1-bromo-3-chlorobenzene (108-37-2) + carbon monoxide (201230-82-2) → methyl 3-chlorobenzoate (2905-65-9)

Conditions	Yield
With benzophenone; sodium methylate; cobalt(II) acetate at 40℃; under 750.075 Torr; for 15h; Irradiation;	97%
With sodium methylate; C2H5OOCCH2Co(CO)4 In diethyl ether at 25 - 35℃;	78%

styrene (292638-84-7) + 1-bromo-3-chlorobenzene (108-37-2) → (E)-3-chlorostilbene (14064-43-8)

Conditions	Yield
With potassium carbonate In methanol; water at 45℃; for 6h; Catalytic behavior; Heck Reaction; Green chemistry; stereoselective reaction;	97%
With CF3O3S(1-)*C52H46NO2P2Pd(1+); potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 0.1h; Heck cross-coupling reaction; In air; Microwave irradiation; chemoselective reaction;	96%
With triethylamine In N,N-dimethyl-formamide for 0.233333h; Sonication;	95%

1-bromo-3-chlorobenzene (108-37-2) + sodium n-propoxide (6819-41-6) → 1-chloro-3-propoxybenzene (51241-31-7)

Conditions	Yield
With propyl methanoate; lithium chloride; copper(I) bromide In propan-1-ol at 110℃; for 4h; Sealed tube;	97%

1-bromo-3-chlorobenzene (108-37-2) + Trimethyl borate (121-43-7) → 3-chlorophenylboronic acid (63503-60-6)

Conditions	Yield
Stage #1: 1-bromo-3-chlorobenzene 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;	97%
Stage #1: 1-bromo-3-chlorobenzene With isopropylmagnesium chloride; lithium chloride; 3-butyl-1-methylimidazolium acetate In tetrahydrofuran at 5 - 10℃; for 3h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #3: With hydrogenchloride In water at 5℃; for 0.5h; Inert atmosphere;	66.43 g

1-bromo-3-chlorobenzene (108-37-2) + 4,6-diphenyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1': 2',1"-terphenyl-3-yl]-1,3,5-triazine → 2-[3-chloro-1,1': 5',1": 2",1""-quaterphenyl-3"-yl]-4,6-diphenyl-1,3,5-triazine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water for 20h; Inert atmosphere; Reflux;	97%

1-bromo-3-chlorobenzene (108-37-2) → PCB 11 (2050-67-1)

Conditions	Yield
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 5h; Microwave irradiation; chemoselective reaction;	96%
With [Pd{C6H2(CH2CH2NH2)-(OMe)2-2,3}(μ-Br)]2; potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 0.0666667h; Microwave irradiation;	96%
With [Pd(C6H4CH2NH2-κ2-CN)PPh3MOBPPY]OTf; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.0333333h; Microwave irradiation; chemoselective reaction;	92%

1-bromo-3-chlorobenzene (108-37-2) + Pentafluorobenzene (363-72-4) → 3'-chloro-2,3,4,5,6-pentafluoro-1,1'-biphenyl (786-55-0)

Conditions	Yield
With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; potassium carbonate; palladium diacetate In N,N-dimethyl acetamide at 120℃;	96%

1-bromo-3-chlorobenzene (108-37-2) + 2-methyl-but-3-yn-2-ol (115-19-5) → 2-methyl-4-(3-chlorophenyl)-3-butyn-2-ol

Conditions	Yield
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; Tri(p-tolyl)phosphine In tetrahydrofuran at 80℃; for 6h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;	96%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 90℃; for 72h; Sonogashira Coupling;	94%

Upstream product

• 585-79-5 m-nitrobromobenzene 
• 873-38-1 4-chloro-2-bromoaniline 
• 7726-95-6 bromine 
• 108-90-7 chlorobenzene 
• 63503-60-6 3-chlorophenylboronic acid 
• 64-19-7 acetic acid 
• 88400-64-0 1-chloro-1,2,3,4,5,6-hexabromocyclohexane 
• 108-88-3 toluene 
• 456-39-3 3-chlorobenzenediazonium tetrafluoroborate 
• 108-43-0 3-monochlorophenol 
• 31928-47-9 4-bromo-2-chloroiodobenzene 
• 31928-44-6 2-bromo-4-chloroiodobenzene 
• 2312-23-4 m-chlorophenylhydrazine hydrochloride 
• 106-39-8 bromochlorobenzene 

Downstream Products

• 72450-95-4 (E)-1-(m-Chlorphenyl)but-1-en-3-in 
• 93040-74-5 5-(3-chlorophenyl)-5-hydroxy-1-methylpyrrolidin-2-one 
• 79419-92-4 3-(3-Chloro-phenyl)-3-hydroxy-2-pyridin-2-yl-2,3-dihydro-isoindol-1-one 
• 79419-93-5 2-(2-Chloro-phenyl)-3-(3-chloro-phenyl)-3-hydroxy-2,3-dihydro-isoindol-1-one 
• 92960-23-1 2-(m-chlorophenyl)-cyclohexanol 
• 99586-30-8 2-bromo-3'-chlorobenzophenone 
• 65-85-0 benzoic acid 
• 535-80-8 3-chlorobenzoate 
• 2051-61-8 m-chlorobiphenyl 
• 5182-44-5 2-(3-chlorophenyl)ethanol 
• 1459-93-4 dimethyl Isophthalate 
• 2905-65-9 methyl 3-chlorobenzoate 
• 21905-97-5 3-(3-chlorophenyl)butan-2-one 
• 321-31-3 1-(3-chlorophenyl)-2,2,2-trifluoroethanone 

Relevant articles and documents

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Metal- and base-free synthesis of aryl bromides from arylhydrazines

An efficient method was developed to synthesize brominated aromatic compounds from arylhydrazine hydrochlorides by using BBr3 in DMSO/CPME (cyclopentyl methyl ether) under air at 80 °C for 1 h without the use of bases or metal catalysts. In particular, this method could be carried out satisfactorily using electron-withdrawing groups to afford aryl bromides in a moderate to excellent yields.

Stereoselective oxidation of alkanes with: M -CPBA as an oxidant and cobalt complex with isoindole-based ligands as catalysts

Two complexes with isoindole-core ligands of general formula [M{C6H4C(NH2)NC(ONCMe2)2}2](NO3)2 (M = Co for 1 and M = Ni for 2) were studied as catalysts for the mild stereoselective alkane oxidation with m-chloroperbenzoic acid (m-CPBA) as an oxidant and cis-1,2-dimethylcyclohexane (cis-1,2-DMCH) as a main model substrate. Complex 1 disclosed a pronounced activity, with high retention of stereoconfiguration of substrates (>98% for cis-1,2-DMCH) and highest cis/trans ratio of tertiary alcohols (products) of 56, under mild conditions. The best achieved yields of tertiary cis-alcohols were of 13.7 and 50.5%, based on the substrate (cis-1,2-DMCH) and the oxidant (m-CPBA) respectively. Kinetic experiments, high bond and stereoselectivity parameters, kinetic isotope effect of 7.2(2) in the oxidation of cyclohexane, and incorporation of 18O from H218O support the involvement of CoIVO high-valent metal-oxo intermediates as main C-H attacking species.