Triphenylphosphine → 2-Ethoxycarbonylbenzyltriphenylphosphonium bromide

HRID 660558Notes

Reaction equation

HRID 660558 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][Br:12])[CH3:2].[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Br-:12].[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][P+:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 11032082Ethyl 2-(bromomethyl)benzoate

Product 1

HCID 190927132-Ethoxycarbonylbenzyltriphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-bromomethylbenzoic acid ethyl ester (25 g, 102.8 mmol) and triphenylphosphine (32.4 g, 123.5 mmol) in toluene is refluxed for 1 h. The solution is cooled to RT and filtered to afford the title compound as a brown solid: (M+1)+=243, 245.

Workup

  1. temperatureis refluxed for 1 h
  2. filtrationfiltered

Sources & evidence

ORD record
ord-4ceab4532bed4b11b07c2f294720dbdb
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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