536-38-9

Basic information

• Product Name: 4-Chloro-2'-bromoacetophenone
• Synonyms: 4-Chlorophenacylbromide 99%;2-Bromo-4'-chloroacetophenone, 98+%;alpha-Bromo-4-chloro;2-Bromo-1-(4-chlorophenyl)ethan-1-one, 2-Bromo-4'-chloroacetophenone;2-BROMO-4''-CHLOROACETOPHENONE(2,4-DICHLOROPENTAPHENONE);2-Bromo-4-chlorlacetophenone;ALPHA-Bromo-4''-chloroacetophenone;2-BROMO-4''-CHLOROACETOPHENONE (4-CHLOROPHENACYL BROMIDE)
• CAS NO: 536-38-9
• Molecular Formula: C₈H₆BrClO
• Molecular Weight: 233.49
• EINECS: 208-631-5
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Aromatics Compounds;Aromatics;Acetophenone series
• Mol File: 536-38-9.mol
• Article Data: 147

Chemical Properties

• Melting Point: 93-96 °C(lit.)
• Boiling Point: 186°C (rough estimate)
• Flash Point: 129 °C
• Appearance: White to pale yellow/Crystals
• Density: 1.5624 (rough estimate)
• Vapor Pressure: 0.00216mmHg at 25°C
• Refractive Index: 1.5963 (estimate)
• Storage Temp.: Keep Cold
• Solubility: soluble in Methanol
• Water Solubility: Insoluble in water.
• Sensitive: Lachrymatory
• Merck: 14,2153
• BRN: 607603
• CAS DataBase Reference: 4-Chloro-2'-bromoacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2'-bromoacetophenone(536-38-9)
• EPA Substance Registry System: 4-Chloro-2'-bromoacetophenone(536-38-9)

Safety Data

• Hazard Codes: C
• Statements: 34-22-36
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 2
• RTECS: AM5978800
• F: 19
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 536-38-9(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Powder

Uses

Different sources of media describe the Uses of 536-38-9 differently. You can refer to the following data:
1. In the preparation of quaternary salts of methenamine and of chlorophenol glyoximes.
2. 2-Bromo-4'-chloroacetophenone is used as pharmaceutical intermediate.

InChI:InChI=1/C8H6BrClO/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4H,5H2

Synthetic route

para-chloroacetophenone (99-91-2) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With pyridinium hydrobromide perbromide; acetic acid at 20℃; for 18h;	99%
With bromine In acetic acid	98%
With hydrogen bromide; bromine; acetic acid In water at 0 - 20℃;	98.67%

1-(bromoethynyl)-4-chlorobenzene (33491-03-1) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With water; copper(II) acetate monohydrate; trifluoroacetic acid at 70℃; for 6h; chemoselective reaction;	93%
With water In 1,2-dichloro-ethane at 20℃; for 14h;	92%
With tetrafluoroboric acid; water In 2,2,2-trifluoroethanol at 80℃; for 2h;	91%

para-chloroacetophenone (99-91-2) → 2,2-dibromo-1-(4-chlorophenyl)ethanone (13651-12-2) + 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With N-Bromosuccinimide; silica gel In methanol for 0.316667h; Reflux; chemoselective reaction;	A n/a B 91%
With trimethylsilyl bromide; potassium nitrate In dichloromethane at 20℃; for 20h;	A n/a B 72%
With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 24h;	A n/a B 89 % Spectr.
With ammonium metavanadate; aluminum tri-bromide; oxygen In acetonitrile at 80℃; for 18h;	A 27 %Spectr. B 70 %Spectr.
With copper(ll) bromide In chloroform; ethyl acetate for 5h; Reflux;

α-bromomethyl-4-chlorostyrene (89220-51-9) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; C65H77N5O4S2; oxygen In 1,2-dichloro-ethane at 75℃; under 760.051 Torr; for 24h; Green chemistry; chemoselective reaction;	91%

1,1-dibromo-1-(4'-chlorophenyl)ethane → 1-(1-bromovinyl)-4-chlorobenzene (89619-10-3) + 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; Inert atmosphere;	A 91% B n/a

4-vinylbenzyl chloride (1073-67-2) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With dipotassium peroxodisulfate; potassium bromide In water at 60℃; for 12h; Green chemistry;	90%
With tris(2,2'-bipyridyl)ruthenium dichloride; Bromoform; [bis(acetoxy)iodo]benzene In 1,4-dioxane at 20℃; for 8h; Reagent/catalyst; Irradiation;	88%
With hydrogen bromide; oxygen In water; ethyl acetate for 5h; Irradiation;	84%

1-(1-bromovinyl)-4-chlorobenzene (89619-10-3) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen In ethylene dibromide at 75℃; under 760.051 Torr; for 16h; Solvent; Green chemistry; chemoselective reaction;	89%

<1-(4-Chlor-phenyl)-ethyl>-benzylether (2040-38-2) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With p-nitrobenzenesulfonamide; hydrogen bromide; oxygen; sodium nitrite In water; acetonitrile at 0 - 60℃; under 760.051 Torr; for 24.5h;	88%

1-(4-chlorophenyl)-2-diazoethanone (3282-33-5) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With ferric(III) bromide; silica gel In dichloromethane at 20℃; for 0.166667h;	85%

4-n-chlorophenylacetylene (873-73-4) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With N,N'-ethylenethiourea; 1,3-dibromo-5,5-dimethylhydantoin; water In acetone at 45℃;	84%
Stage #1: 4-n-chlorophenylacetylene With methanol; gold(III) chloride; silver(I) triflimide In 1,4-dioxane at 45℃; Stage #2: With N-Bromosuccinimide In 1,4-dioxane regioselective reaction;	75%
Multi-step reaction with 2 steps 1: dibromamine-T; water / acetone / 0.17 h 2: water; sodium sulfite / acetone; ethyl acetate / 20 °C View Scheme

C15H14BrClO → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With p-nitrobenzenesulfonamide; hydrogen bromide; oxygen; sodium nitrite In water; acetonitrile at 0 - 60℃; under 760.051 Torr; for 24.5h;	84%

2,2,2-tribromo-1-(4-chlorophenyl)ethan-1-one (52119-96-7) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With water; hydrogen bromide In tetrahydrofuran at 120℃;	83%

1-(p-chlorophenyl)ethyl alcohol (3391-10-4) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With Oxone; ammonium bromide In methanol; water at 20℃; for 24h; Green chemistry;	81%
With N-Bromosuccinimide In tetrahydrofuran at 20℃;

C16H17ClO2 → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With p-nitrobenzenesulfonamide; hydrogen bromide; oxygen; sodium nitrite In water; acetonitrile at 0 - 50℃; under 760.051 Torr; for 24.5h;	80%

4-vinylbenzyl chloride (1073-67-2) → 2-bromo-1-(4-chlorophenyl)ethanol (6314-52-9) + 1,2-dibromo-1-(4-chlorophenyl)ethane (23135-16-2) + 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With sodium bromate; sulfuric acid; sodium bromide In 1,4-dioxane; water at 20℃; for 6.5h;	A 12% B 2% C 77%

4-chloro(ethylbenzene) (622-98-0) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With hydrogen bromide; oxygen In water; ethyl acetate at 20℃; for 10h; Irradiation;	66%

4-chloro(ethylbenzene) (622-98-0) + ethyl acetate (141-78-6) → 2,2-dibromo-1-(4-chlorophenyl)ethanone (13651-12-2) + 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With water; hydrogen bromide; oxygen for 7h; Irradiation;	A 26% B 45%

ethanol (64-17-5) + 2,2-dibromo-1-(4-chlorophenyl)ethanone (13651-12-2) → ethyl 2-(4-chlorophenyl)-2-oxoacetate (34966-48-8) + 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
for 20h; Inert atmosphere; Irradiation;	A 26% B 22%

4-chloro(ethylbenzene) (622-98-0) + ethyl acetate (141-78-6) → ethyl 2-(4-chlorophenyl)-2-oxoacetate (34966-48-8) + 4-chlorophenylglyoxylic acid (7099-88-9) + 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With water; hydrogen bromide; oxygen for 20h; Irradiation;	A 64 %Spectr. B 10% C 11%

2-bromoacetyl chloride (22118-09-8) + chlorobenzene (108-90-7) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With aluminium trichloride
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 2h; Friedel-Crafts Acylation;

4-chloro-α-bromoacetophenone methyl hemiacetal (119205-36-6) → methanol (67-56-1) + 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With hydrogen cation In water at 25℃; Rate constant;
With water at 25℃; Rate constant;
With hydroxide In water at 25℃; Rate constant;
With acetate In water at 25℃; Rate constant;

2,2-dibromo-1-(4-chlorophenyl)ethanone (13651-12-2) → 3,5-bis(4-chlorobenzoyl)-1,2,4-thiadiazole (146692-13-9) + 4-chlorobenzoylmethyl bromide (536-38-9) + 3-(4-chlorobenzoylformamido)-4-(4-chlorophenyl)-1,2,5-thiadiazole (163430-76-0)

Conditions	Yield
With tetrasulphur tetranitride at 115℃; for 10h;	A 2 % Turnov. B 100 mg C 12 % Turnov.

etheric solution of 1-<4-chloro-phenyl>-ethanone-(1) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With aluminium trichloride; bromine

1-(p-chlorophenyl)ethyl alcohol (3391-10-4) → 2-bromo-1-(4-chlorophenyl)ethanol (6314-52-9) + para-chloroacetophenone (99-91-2) + 1-(1-bromoethyl)-4-chlorobenzene (14804-61-6) + 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With para-chloroacetophenone; aluminum tri-tert-butoxide; pyridinium hydrobromide perbromide In toluene at 60℃; for 24h; Title compound not separated from byproducts;

2-bromo-1-(4-chlorophenyl)ethanol (6314-52-9) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With dihydrogen peroxide In 1,4-dioxane; water at 25℃; for 10h;

1-(p-chlorophenyl)ethyl alcohol (3391-10-4) → para-chloroacetophenone (99-91-2) + 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With sodium bromate; sulfuric acid; sodium bromide In water at 60℃; for 0.166667h; Microwave irradiation;

4-chloro(ethylbenzene) (622-98-0) → 2,2-dibromo-1-(4-chlorophenyl)ethanone (13651-12-2) + 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With carbon tetrabromide; hydrogen bromide; oxygen In dichloromethane; water for 10h; Irradiation;	A 6 %Spectr. B 48 %Spectr.

1,2-dibromo-1-(4-chlorophenyl)ethane (23135-16-2) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions

Yield

Multi-step reaction with 2 steps 1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water / 24 h / 70 °C 2: iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen / ethylene dibromide / 16 h / 75 °C / 760.05 Torr / Green chemistry View Scheme

2,2-dibromo-1-(4-chlorophenyl)ethanone (13651-12-2) → 4-chlorobenzoylmethyl bromide (536-38-9)

Conditions	Yield
With water; sodium sulfite In ethyl acetate; acetone at 20℃;	180 mg

thiourea (17356-08-0) + 4-chlorobenzoylmethyl bromide (536-38-9) → 4-(4-chlorophenyl)-2-thiazolamine (2103-99-3)

Conditions	Yield
In ethanol at 70℃; for 1h;	100%
In ethanol at 70℃; for 1h; Hantzsch Thiazole Synthesis;	100%
With sodium fluoride In methanol; water at 20℃; for 0.0166667h; Reagent/catalyst; Solvent;	99%

potassium cyanamide salt (29422-34-2) + 4-chlorobenzoylmethyl bromide (536-38-9) → (4-Amino-2-ethoxy-thiazol-5-yl)-(4-chloro-phenyl)-methanone (86690-08-6)

Conditions	Yield
With triethylamine In acetone for 2h; Ambient temperature;	100%

4-chlorobenzoylmethyl bromide (536-38-9) + ((4-chlorophenyl)amino)((2-phenylethyl)amino)methane-1-thione (93360-14-6) → (4-Chloro-phenyl)-[4-(4-chloro-phenyl)-3-phenethyl-3H-thiazol-(2Z)-ylidene]-amine; hydrobromide

Conditions	Yield
In ethanol for 4h; Heating;	100%

2,6-dimethyl-1,5-dihydroxynaphthalene (123979-29-3) + 4-chlorobenzoylmethyl bromide (536-38-9) → 2,6-dimethyl-1,5-bis-1-(4-chlorophenyl)-1-oxo-2-ethoxy)naphthalene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	100%

2-Iodophenol (533-58-4) + 4-chlorobenzoylmethyl bromide (536-38-9) → 1-(4-chlorophenyl)-2-(2-iodophenoxy)ethan-1-one

Conditions	Yield
With potassium carbonate In acetone at 80℃; for 4h;	100%
With potassium carbonate In acetone Heating;
With potassium carbonate In acetone Heating;
With potassium carbonate In acetone at 60℃;	3.39 g

(phenylaminothioyl)ethyl carbamate Wang resin + 4-chlorobenzoylmethyl bromide (536-38-9) → N-[3-(2-aminoethyl)-4-(4-chlorophenyl)-1,3-thiazol-2(3H)-ylidene]aniline

Conditions	Yield
Stage #1: (phenylaminothioyl)ethyl carbamate Wang resin; 4-chlorobenzoylmethyl bromide In 1,2-dimethoxyethane at 80℃; for 2h; Stage #2: With trifluoroacetic acid In dichloromethane for 1.5h; Stage #3: With aluminum oxide In methanol	100%

4-{[(phenylethylamino)carbothioyl]amino}-phenylethyl carbamate Wang resin + 4-chlorobenzoylmethyl bromide (536-38-9) → 4-(2-aminoethyl)-N-[4-(4-chlorophenyl)-3-phenethyl-1,3-thiazol-2(3H)-ylidene]aniline

Conditions	Yield
Stage #1: 4-{[(phenylethylamino)carbothioyl]amino}-phenylethyl carbamate Wang resin; 4-chlorobenzoylmethyl bromide In DMF (N,N-dimethyl-formamide) at 80℃; for 2h; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1.5h; Stage #3: With aluminum oxide In methanol	100%

(R)-2-thiocarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (1089729-72-5) + 4-chlorobenzoylmethyl bromide (536-38-9) → (R)-2-[4-(4-chloro-phenyl)-thiazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1089729-73-6)

Conditions	Yield
Stage #1: (R)-2-thiocarbamoyl-piperidine-1-carboxylic acid tert-butyl ester; 4-chlorobenzoylmethyl bromide With sodium hydrogencarbonate In 1,2-dimethoxyethane at 20℃; for 24h; Stage #2: With pyridine; trifluoroacetic anhydride In 1,2-dimethoxyethane at 0 - 20℃; for 0.5h;	100%

isoquinoline (119-65-3) + 4-chlorobenzoylmethyl bromide (536-38-9) → 2-(2-(4-chlorophenyl)-2-oxoethyl)isoquinolin-2-ium bromide (57269-96-2)

Conditions	Yield
In acetonitrile at 20℃; for 0.333333h;	100%
In dichloromethane at 20℃; for 24h;
With cetyltrimethylammonim bromide In water at 20℃; for 0.5h;

2-methylpropan-2-thiol (75-66-1) + 4-chlorobenzoylmethyl bromide (536-38-9) → C12H15ClOS (88577-88-2)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 16h;	100%

tert-butyl 4-carbamothioylpiperidine-1-carboxylate (214834-18-1) + 4-chlorobenzoylmethyl bromide (536-38-9) → tert-butyl 4-(4-(4-chlorophenyl)thiazol-2-yl)piperidine-1-carboxylate

Conditions	Yield
In ethanol at 80℃; for 1h;	100%
In N,N-dimethyl-formamide at 20℃; for 2h;
In ethanol Hantzsch Thiazole Synthesis; Reflux;

4-chlorobenzoylmethyl bromide (536-38-9) + 2-hydroxyethanethiol (60-24-2) → C10H11ClO2S (1157217-46-3)

Conditions	Yield
at 20℃; for 18h;	100%

4-chlorobenzaldehyde thiosemicarbazone (5706-80-9) + 4-chlorobenzoylmethyl bromide (536-38-9) → 1-(4-chlorobenzylidene)-2-[4-(4-chlorophenyl)thiazol-2-yl]hydrazine

Conditions	Yield
In isopropyl alcohol Reflux;	100%

2-(N-t-butoxycarbonylamino)thioacetamide (89226-13-1) + 4-chlorobenzoylmethyl bromide (536-38-9) → [4-(4-chlorophenyl)thiazol-2-yl]methylamine hydrochloride

Conditions	Yield
Stage #1: 2-(N-t-butoxycarbonylamino)thioacetamide; 4-chlorobenzoylmethyl bromide In ethanol at 20℃; Stage #2: With hydrogenchloride In 1,4-dioxane; ethanol at 20℃; for 2h;	100%

4-chlorobenzoylmethyl bromide (536-38-9) + 4-methyl-N-{2-(phenylethynyl)phenyl}benzenesulfonamide (442155-91-1) → N-(2-(4-chlorophenyl)-2-oxoethyl)-4-methyl-N-(2-(phenylethynyl)phenyl)benzenesulfonamide

Conditions	Yield
Stage #1: 4-methyl-N-{2-(phenylethynyl)phenyl}benzenesulfonamide With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 4-chlorobenzoylmethyl bromide In N,N-dimethyl-formamide at 20℃;	100%
Stage #1: 4-methyl-N-{2-(phenylethynyl)phenyl}benzenesulfonamide With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 4-chlorobenzoylmethyl bromide In N,N-dimethyl-formamide at 20℃;	77%

C16H25N3OS + 4-chlorobenzoylmethyl bromide (536-38-9) → (E)-2,6-di-tert-butyl-4-((2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazono)methyl) phenol

Conditions	Yield
	100%

selenosemicarbazide (21198-79-8) + 4-chlorobenzoylmethyl bromide (536-38-9) → 2-imino-5-(4-chlorophenyl)-6H-1,3,4-selenadiazine

Conditions	Yield
Stage #1: selenosemicarbazide; 4-chlorobenzoylmethyl bromide In ethanol at 20℃; Reflux; Stage #2: With ammonium hydroxide In ethanol pH=8;	100%

4-chlorobenzoylmethyl bromide (536-38-9) + quinidine (56-54-2) → C28H30ClN2O3(1+)*Br(1-)

Conditions	Yield
In tetrahydrofuran Inert atmosphere;	100%

(piperidin-4-yl)carbamic acid tert-butyl ester (73874-95-0) + 4-chlorobenzoylmethyl bromide (536-38-9) → tert-butyl (1-(2-(4-chlorophenyl)-2-oxoethyl)piperidin-4-yl)carbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 90℃; Sealed tube;	100%

2-aminopyridine (504-29-0) + 4-chlorobenzoylmethyl bromide (536-38-9) → 2-(4-chlorophenyl)imidazolo[1,2-a]pyridine (38922-74-6)

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	99%
Stage #1: 2-aminopyridine; 4-chlorobenzoylmethyl bromide In ethanol for 3h; Reflux; Stage #2: With sodium hydrogencarbonate In ethanol for 4h; Reflux;	96%
In water; isopropyl alcohol at 75℃; Microwave irradiation; Green chemistry;	95%

2-Amino-4-methylpyridine (695-34-1) + 4-chlorobenzoylmethyl bromide (536-38-9) → 2-(4-chlorophenyl)-7-methyl-imidazo[1,2-a]pyridine (65964-62-7)

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	99%
With sodium hydrogencarbonate In ethanol for 20h; Reflux;	79%
With ethanol
With sodium carbonate In ethanol for 1h; Reflux;

4-chlorobenzoylmethyl bromide (536-38-9) → 1-(2-bromo-1-chloroethyl)-4-chlorobenzene (109275-35-6)

Conditions	Yield
With indium(III) hydroxide; dimethylmonochlorosilane In chloroform at 20℃; for 4h;	99%

4-chlorobenzoylmethyl bromide (536-38-9) + 3-[1-Dimethylamino-meth-(E)-ylidene]-1,1-diethyl-thiourea → 5-(4'-chlorobenzoyl)-2-N,N-diethylamino-1,3-thiazole

Conditions	Yield
In tetrahydrofuran for 2h; Heating;	99%

4-Methoxybenzenethiol (696-63-9) + 4-chlorobenzoylmethyl bromide (536-38-9) → 1-(4-chlorophenyl)-2-[(4-methoxyphenyl)sulfanyl]-1-ethanone

Conditions	Yield
With triethylamine In ethanol at 20℃;	99%
With potassium hydroxide In methanol; water at 15℃; for 1h;

papaveraldine (522-57-6) + 4-chlorobenzoylmethyl bromide (536-38-9) → p-chlorophenacylpapaveraldinium bromide

Conditions	Yield
In acetone for 360h; Heating;	99%

4-chlorobenzoylmethyl bromide (536-38-9) + 2-methylcyclohexylidene-thiosemicarbazone → C16H18ClN3S (1049014-19-8)

Conditions	Yield
In isopropyl alcohol at 20℃; for 2h;	99%
In ethanol at 20℃; Hantzsch reaction;
Stage #1: 4-chlorobenzoylmethyl bromide; 2-methylcyclohexylidene-thiosemicarbazone In methanol for 0.0166667h; Hantzsch Thiazole Synthesis; Stage #2: In methanol at 90℃; for 0.166667h; Hantzsch Thiazole Synthesis; Microwave irradiation;

4-pentafluorosulfanylbenzoselenoamide (1597437-97-2) + 4-chlorobenzoylmethyl bromide (536-38-9) → 4-(4′-chlorophenyl)-2-(4″-pentafluorosulfanylphenyl)-1,3-selenazole (1597437-98-3)

Conditions	Yield
In ethanol for 2h; Reflux; Inert atmosphere; Schlenk technique;	99%

1-methyl-1H-indole-2,3-dione (2058-74-4) + 4-chlorobenzoylmethyl bromide (536-38-9) → (E)-3’-(4-chlorobenzoyl)-1-methylspiro[indoline-3,2’-oxiran]-2-one

Conditions	Yield
With potassium carbonate In ethanol at 20℃; Darzens Condensation;	99%

4-chlorobenzoylmethyl bromide (536-38-9) + saccharin (81-07-2) → 2-[2-(4-chlorophenyl)-2-oxoethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (41335-62-0)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 10h;	99%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 9h;
With triethylamine In N,N-dimethyl-formamide

Upstream product

• 99-91-2 para-chloroacetophenone 
• 13651-12-2 2,2-dibromo-1-(4-chlorophenyl)ethanone 
• 1073-67-2 4-vinylbenzyl chloride 
• 6314-52-9 2-bromo-1-(4-chlorophenyl)ethanol 
• 3391-10-4 1-(p-chlorophenyl)ethyl alcohol 
• 119205-36-6 4-chloro-α-bromoacetophenone methyl hemiacetal 
• 22118-09-8 2-bromoacetyl chloride 
• 108-90-7 chlorobenzene 
• 128-08-5 N-Bromosuccinimide 
• 92617-56-6 2,2,2-tribromo-1-(4-chlorophenyl)methanol 
• 104-88-1 4-chlorobenzaldehyde 
• 52119-96-7 2,2,2-tribromo-1-(4-chlorophenyl)ethan-1-one 
• 106-39-8 bromochlorobenzene 
• 3282-33-5 1-(4-chlorophenyl)-2-diazoethanone 

Downstream Products

• 20099-95-0 1-(4-chlorophenyl)-2-(4-morpholinyl)ethanone 
• 26031-66-3 1-(2-(4-chlorophenyl)-2-oxoethyl)pyridinium bromide 
• 82746-43-8 1-(2-(4-chlorophenyl)-2-oxoethyl)-2-methylpyridinium bromide 
• 108800-05-1 1-(4-chloro-phenacyl)-3-hydroxy-pyridinium; bromide 
• 7401-14-1 2-chloro-1-[2-(4-chlorophenyl)-2-oxoethyl]pyridinium bromide 
• 7511-99-1 3-bromo-1-(4-chloro-phenacyl)-pyridinium; bromide 
• 88964-99-2 6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine 
• 6273-38-7 3-bromo-1-(4-chloro-phenacyl)-quinolinium; bromide 
• 6273-37-6 6-chloro-1-(4-chloro-phenacyl)-quinolinium; bromide 
• 93994-39-9 1-(p-chlorophenacyl)-4-phenylpiperazine 
• 5467-71-0 4-chlorophenacylamine hydrochloride 
• 122262-55-9 2-(4-chloro-phenyl)-3-hydroxy-quinoline-4-carboxylic acid 
• 122262-53-7 6-chloro-2-(4-chloro-phenyl)-3-hydroxy-quinoline-4-carboxylic acid 
• 60532-55-0 1-(4-chloro-phenyl)-2-p-toluidino-ethanone 

Relevant articles and documents

Synthesis of novel thiazolo[2,3-b]quinazolines by cyclization reaction of octahydroquinazoline-2-thiones with α-bromoketones

Novel thiazolo[2,3-b]quinazolines were prepared by the cyclization reaction between octahydroquinazoline-2-thiones with α-bromoketones, which provides a readily accessible multifunctionalized quinazoline template for diversity-oriented synthesis. 2011 · Copyright by Walter de Gruyter.

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.

Solvent-free preparation of α,α-dichloroketones with sulfuryl chloride

An efficient and facile method is reported for the synthesis of a series of α,α-dichloroketones. The direct dichlorination of methyl ketones and 1,3-dicarbonyls using an excess amount of sulfuryl chloride affords the corresponding gem-dichloro compounds in moderate to excellent yields. Moreover, the protocol features high yields, broad substrate scope, and simple reaction conditions without using any catalysts and solvents.