Water → 2-Bromo-1-(3,4-dichlorophenyl)ethanone

HRID 248907

Reaction equation

HRID 248907 reaction equation
[Br:1]Br.[CH3:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)=[O:5].[Al+3].[Cl-].[Cl-].[Cl-].O>C(OCC)C>[Cl:13][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[Cl:12])[C:4](=[O:5])[CH2:3][Br:1]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 75841Ethanone, 1-(3,4-dichlorophenyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Bromine in a quantity of 10.2 ml (0.2 mol) is added dropwise to a mixture of 37.8 g 3.4-dichloroacetophenone and approx. 1.0 g anhydrous AlCl3 in 600 ml dry diethylether while stirring and cooling in ice. After stirring for 0.5 hr at 0° C. and 1.5 hr at room temperature, 30 ml water are added slowly. The organic phase is separated, washed twice with water, dried and evaporated to dryness. A small amount of petroleum ether (40-60) is added to the residue and the mixture is stirred at approx. 0° C. The desired 3.4-dichlorophenacylbromide is obtained as a crystalline material in a yield of 39.8 g (74%); melting point 55°-58° C.; TLC (CH2Cl2)=0.5.

Workup

  1. temperaturecooling in ice
  2. stirringAfter stirring for 0.5 hr at 0° C. and 1.5 hr at room temperature
  3. customThe organic phase is separated
  4. washwashed twice with water
  5. customdried
  6. customevaporated to dryness
  7. additionA small amount of petroleum ether (40-60) is added to the residue
  8. stirringthe mixture is stirred at approx. 0° C

Sources & evidence

ORD record
ord-8cc3378f8f4c456abf138b1e58aecd9c
Source dataset
uspto-grants-1993_05
Patent number
US05212197

Linked notes

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