Triphenylphosphine → {[4-(Ethoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromide

HRID 2296044Notes

Reaction equation

HRID 2296044 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][C:22]1[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=1>C1C=CC=CC=1>[Br-:20].[CH2:29]([O:28][C:26]([C:25]1[CH:24]=[CH:23][C:22]([CH2:21][P+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:32][CH:31]=1)=[O:27])[CH3:30]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 954261Ethyl 4-(bromomethyl)benzoate

Product 1

HCID 16236583{[4-(Ethoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromideYield 74.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 16 g of triphenylphosphine, 13.35 g of ethyl 4-bromomethylbenzoate and 50 ml of benzene was stirred at room temperature for 2 days. The precipitate was filtered off, and dried in vacuo to give 20.8 g of (4-ethoxycarbonylbenzyl)triphenylphosphonium bromide.

Workup

  1. filtrationThe precipitate was filtered off
  2. customdried in vacuo

Sources & evidence

ORD record
ord-10f1ae07c4b845d0a06a06658e9c4870
Source dataset
uspto-grants-1984_01
Patent number
US04427682

Reaction notes

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