Acetic Acid → Phenacyl bromide

HRID 7096

Reaction equation

HRID 7096 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(O)(=O)C.[Br:14]Br>>[Br:14][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7410AcetophenoneHCID 24408Bromine

Product 1

HCID 6259Phenacyl bromideYield 41%

Procedure

Reaction of acetophenone (5.0 g, 42.00 mmol), acetic acid (2.4 mL, 42.00 mmol), and bromine (2.5 mL, 48.00 mmol) followed by recrystallisation from cold EtOAc/Hexane gave the title compound (3.4 g, 41%) as a white crystal. 1H NMR (300 MHz, CDCl3) δ 4.47 (s, 2H), 7.51 (d, 2H, J=7.5 Hz), 7.63 (t, 1H, J=7.5 Hz), 8.00 (d, 2H, J=7.2 Hz).

Workup

  1. customfollowed by recrystallisation from cold EtOAc/Hexane

Sources & evidence

ORD record
ord-9651c158160d4c42a424784a20c7783a
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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