Phenacyl bromide → (2-Oxo-2-phenylethyl)(triphenyl)phosphanium bromide

HRID 232111Notes

Reaction equation

HRID 232111 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Br-:1].[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][P+:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 11776Triphenylphosphine

Product 1

HCID 197064(2-Oxo-2-phenylethyl)(triphenyl)phosphanium bromideYield 93.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50.0 g. (251 mmoles) of α-bromoacetophenone (Compound CI) and 65.9 g. (251 mmoles) of triphenylphosphine are stirred in 500 ml. of toluene at 20°-25° C. under nitrogen for 16 hours, and the resulting solid is collected by filtration, rinsed with toluene and rinsed with diethyl ether to obtain the product as a white powder (107.98 g. (93%)).

Workup

  1. filtrationthe resulting solid is collected by filtration
  2. washrinsed with toluene
  3. washrinsed with diethyl ether

Sources & evidence

ORD record
ord-ad35852fac2f49d28011b407b1a9b7b1
Source dataset
uspto-grants-1989_07
Patent number
US04851427

Reaction notes

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