Toluene → (3-Bromopropyl)-triphenylphosphonium bromide hydrobromide

HRID 1196986Notes

Reaction equation

HRID 1196986 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][C:21]([Br:24])([CH3:23])C.[C:25]1(C)C=CC=CC=1>>[BrH:20].[Br-:20].[Br:24][CH2:21][CH2:23][CH2:25][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 116582,2-DibromopropaneHCID 11776Triphenylphosphine

Product 1

HCID 19897085(3-Bromopropyl)-triphenylphosphonium bromide hydrobromide

Procedure

In this example, 350.0 g of triphenylphosphine and 270.0 g of dibromopropane are suspended in 700 ml of toluene and the suspension is heated at reflux for 25 hours. After allowing the suspension to stand for cooling, the formed product is separated by filtration and washed with 2 l of toluene to obtain 550.0 g of (3-bromopropyl)-triphenylphosphonium bromide hydrobromide having m.p. 233-234° C.

Workup

  1. temperaturethe suspension is heated
  2. temperatureat reflux for 25 hours
  3. temperaturefor cooling
  4. customthe formed product is separated by filtration
  5. washwashed with 2 l of toluene

Sources & evidence

ORD record
ord-9d5712f1c57043949b45747e036ef47c
Source dataset
uspto-grants-1992_05
Patent number
US05116863

Reaction notes

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