Toluene → (4-Phenylbutyl)triphenylphosphonium bromide

HRID 1576942Notes

Reaction equation

HRID 1576942 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][Br:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC=CC=1>CCOCC>[Br-:11].[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P+:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 2596681-Bromo-4-phenylbutane

Product 1

HCID 18187515(4-Phenylbutyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 145 g. of 4-phenyl-1-bromobutane and 179 g. of triphenylphosphine in 350 ml. of toluene is heated at reflux under nitrogen for 16 hours. The mixture is then cooled slowly and ether is added giving a precipitate of (4-phenylbutyl)triphenylphosphonium bromide which is washed thoroughly with benzene/ether and dried 18 hours at 50° C. under reduced pressure, 268 g., m.p. 139°-140° C.

Workup

  1. temperatureat reflux under nitrogen for 16 hours
  2. temperatureThe mixture is then cooled slowly

Sources & evidence

ORD record
ord-e6cafe3899aa4302b5612ae9beb50157
Source dataset
uspto-grants-1976_09
Patent number
US03983157

Reaction notes

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