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

HRID 274341Notes

Reaction equation

HRID 274341 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>C(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>[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-oneYield 100%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 6212ChloroformSolvent

Procedure

4'-chloropropiophenone (39.6 g) and anhydrous aluminum chlorid (0.1 g) were dissolved in 100 ml of chloroform. To the resulting solution was protionwise added bromine (37.6 g) at a temperature of 30° to 35° C. The reaction mixture was stirred at room temperature for 30 minutes. Then nitrogen was blown into the reaction mixture to remove the formed hydrogen bromide therefrom. Thereafter, the solvent was distilled off under reduced pressure to give 2-bromo-4'-chloropropiophenone (58.1 g). mp 77.5°-79.5° C.

Workup

  1. customat a temperature of 30° to 35° C
  2. customto remove the formed hydrogen bromide
  3. distillationThereafter, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e7e3e66bcd3044e68b419873ba254cb4
Source dataset
uspto-grants-1995_02
Patent number
US05389648

Reaction notes

Loading…