P-Chloroacetophenone → p-Chlorophenacyl bromide

HRID 908092Notes

Reaction equation

HRID 908092 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C1C=C[NH+:14]=CC=1.[Br:17][Br-]Br>C(O)(=O)C>[ClH:1].[NH2:14][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:10].[Br:17][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:10]

Participants

4

Reactant 1

HCID 7467P-Chloroacetophenone

Product 2

HCID 68303p-Chlorophenacyl bromideHCID 27982112-Amino-1-(4-chlorophenyl)ethan-1-one hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

The starting 2-amino-1-(4-chlorophenyl)ethanone hydrochloride was prepared according to the following procedure. The 1-(4-chlorophenyl)ethanone (1.0 eq.) was dissolved in glacial acetic acid (1 ml, per mmol). To this was added a slurry of pyridinium bromide perbromide (1.03 eq.) in acetic acid (1 mL per mmol). The heterogeneous mixture was stirred for 4 h at ambient temperature. After about 30 min. the mixture turned homogeneous. After pouring into ice-water a yellow precipitate was filtered off and washed with water (2×1 mL per mmol of starting ketone). Drying of the precipitate afforded 2-bromo-1-(4-chlorophenyl)ethanone in ca. 90% yield.

Workup

  1. waitAfter about 30 min. the mixture turned homogeneous
  2. filtrationwas filtered off
  3. washwashed with water (2×1 mL per mmol of starting ketone)
  4. customDrying of the precipitate

Sources & evidence

ORD record
ord-c36b39ac91384ba699e4e403ccd48175
Source dataset
uspto-grants-2011_09
Patent number
US08017555B2

Reaction notes

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