4'-Chloropropiophenone → 2-Bromo-1-(4-chlorophenyl)propan-1-one

HRID 660863Notes

Reaction equation

HRID 660863 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.[Br:12]Br>ClCCl.Br>[Br:12][CH:9]([CH3:10])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)=[O:11]

Participants

5

Reactant 2

HCID 226974'-ChloropropiophenoneHCID 24408Bromine

Product 1

HCID 37882192-Bromo-1-(4-chlorophenyl)propan-1-one

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

3000 mg (17.791 mmol) of 1-(4-chlorophenyl)propan-1-one are placed in 15 ml dichloromethane and treated with one drop of hydrobromic acid. The mixture is stirred at 35° C., then 2843 mg (17.791 mmol) of bromine are added dropwise so that the reaction solution decolorizes again after each addition. Three hours after the start of the reaction, the mixture is evaporated to dryness. 4490 mg (96% of theory) of the target compound are obtained.

Workup

  1. additionafter each addition
  2. customThree hours after the start of the reaction
  3. customthe mixture is evaporated to dryness
  4. custom4490 mg (96% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-5804ae4831a5411aa350e8d72d680bd0
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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