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

HRID 1443536Notes

Reaction equation

HRID 1443536 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]([C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][C:9]=1[Cl:10]>CO>[Br:1][CH2:12][C:11]([C:6]1[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=1)=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 75841Ethanone, 1-(3,4-dichlorophenyl)-

Product 1

HCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

43.9 g (0.275 mol) of bromine was added dropwise to a solution of 50.5 g (0.267 mol) of 3′,4′-dichloro acetophenone in 120 g of methanol at a reaction temperature of 50 to 55° C. After the addition was complete, the methanol was evaporated off the reaction solution under reduced pressure. The resultant concentrate was dissolved in 120 g of toluene and was then washed with water (150 ml×3 times). Thereafter, the toluene was evaporated off under reduced pressure, giving 68.0 g (0.254 mol) of crude brown oily 2-bromo-3′,4′-dichloroacetophenone.

Workup

  1. additionAfter the addition
  2. customthe methanol was evaporated off the reaction solution under reduced pressure
  3. concentrationThe resultant concentrate
  4. dissolutionwas dissolved in 120 g of toluene
  5. washwas then washed with water (150 ml×3 times)
  6. customThereafter, the toluene was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-ff59c1e7df884b249df0d77616dfcf91
Source dataset
uspto-grants-2010_02
Patent number
US07661577B2

Reaction notes

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