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

HRID 1443540Notes

Reaction equation

HRID 1443540 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]([C:11](=[O:14])[CH2:12][CH3:13])[CH:7]=[CH:8][C:9]=1[Cl:10]>CO>[Br:1][CH:12]([CH3:13])[C:11]([C:6]1[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=1)=[O:14]

Participants

4

Reactant 2

HCID 24408BromineHCID 5995981-(3,4-Dichlorophenyl)-1-propanone

Product 1

HCID 134353622-Bromo-1-(3,4-dichlorophenyl)propan-1-oneYield 95.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

51.1 g (0.320 mol) of bromine was added dropwise to a solution of 65.0 g (0.320 mol) of 3′,4′-dichloropropiophenone in 150 g of methanol at a reaction temperature of 58 to 60° C. After the addition was complete, the methanol was evaporated off from the reaction solution under reduced pressure. The resultant concentrate was dissolved in 130 g of toluene and then washed with water (150 ml×3 times). Thereafter, the toluene was evaporated off under reduced pressure, giving 86.6 g (0.307 mol) of crude brown oily 2-bromo-3′,4′-dichloropropiophenone.

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 130 g of toluene
  5. washwashed with water (150 ml×3 times)
  6. customThereafter, the toluene was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-846bca5c21794177870d112cd96e1966
Source dataset
uspto-grants-2010_02
Patent number
US07661577B2

Reaction notes

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