2',4'-Dichloroacetophenone → 2-Bromo-1-(2,4-dichlorophenyl)ethan-1-one

HRID 1443534Notes

Reaction equation

HRID 1443534 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11](=[O:13])[CH3:12]>CO>[Br:1][CH2:12][C:11]([C:5]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=1[Cl:3])=[O:13]

Participants

4

Reactant 2

HCID 166932',4'-DichloroacetophenoneHCID 24408Bromine

Product 1

HCID 758282-Bromo-1-(2,4-dichlorophenyl)ethan-1-oneYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

43.4 g (0.267 mol) of bromine was added dropwise to a solution of 50.5 g (0.267 mol) of 2′,4′-dichloroacetophenone in 100 g of methanol at a reaction temperature of 45 to 50° C. After the addition was complete, the methanol was evaporated off from the reaction solution under reduced pressure. The resultant concentrate was dissolved in 120 g of toluene and was then washed with water (100 ml×3 times). Thereafter, the toluene was distilled off under reduced pressure, giving 68.0 g (0.254 mol) of crude brown oily 2-bromo-2′,4′-dichloroacetophenone.

Workup

  1. additionAfter the addition
  2. customthe methanol was evaporated off from the reaction solution under reduced pressure
  3. concentrationThe resultant concentrate
  4. dissolutionwas dissolved in 120 g of toluene
  5. washwas then washed with water (100 ml×3 times)
  6. distillationThereafter, the toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1b070d83afbd4fd1b9e2f6fa74f712ae
Source dataset
uspto-grants-2010_02
Patent number
US07661577B2

Reaction notes

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