p-Bromoacetophenone → 4-Bromophenacyl bromide

HRID 1500509Notes

Reaction equation

HRID 1500509 reaction equation
[Br:1]Br.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1>ClCCl>[Br:1][CH2:11][C:10]([C:7]1[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][CH:6]=1)=[O:12]

Participants

4

Reactant 2

HCID 7466p-BromoacetophenoneHCID 24408Bromine

Product 1

HCID 74544-Bromophenacyl bromideYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (80 g, 500 mmol) was added dropwise to a solution of 1-(4-bromo-phenyl)-ethanone (100 g, 500 mmol) in dichloromethane (1500 mL) at ambient temperature. The reaction mixture was stirred for 3 h and then concentrated. The residue was washed with dichloromethane (100 mL) to give the crude title compound (120 g, 86% yield) as a white solid. 1H NMR (CDCl3, 400 MHz) δ (ppm): 7.78 (d, J=8.4 Hz, 2H), 7.57 (d, J=8.4 Hz, 2H), 4.32 (s, 2H).

Workup

  1. concentrationconcentrated
  2. washThe residue was washed with dichloromethane (100 mL)

Sources & evidence

ORD record
ord-9ff7908dfa2e4bbabf947f07f0d3a9b4
Source dataset
uspto-grants-2015_12
Patent number
US09206159B2

Reaction notes

Loading…