Triphenylphosphine → 3-Phenylpropyl triphenylphosphonium bromide

HRID 845246Notes

Reaction equation

HRID 845246 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[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>>[Br-:1].[C:5]1([CH2:4][CH2:3][CH2:2][P+:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 11776TriphenylphosphineHCID 12503(3-Bromopropyl)benzene

Product 1

HCID 109286473-Phenylpropyl triphenylphosphonium bromideYield 96%

Conditions

Temperature
100 °C

Procedure

A magnetically stirred suspension of 1bromo-3-phenylpropane (Aldrich, 13.7 ml, 90 mmol) and triphenylphosphine (47.2 g, 180 mmole) was heated at 100° C. (Oil bath) for 2.0 hours. The resulting while solid was then cooled and triturated with ether (5X) to remove most of the unreacted triphenylphosphine, to give Part A(1) compound in 96% yield (wt. 40.0 g).

Workup

  1. temperatureThe resulting while solid was then cooled
  2. customtriturated with ether (5X)
  3. customto remove most of the unreacted triphenylphosphine
  4. customto give Part A(1) compound in 96% yield (wt. 40.0 g)

Sources & evidence

ORD record
ord-6ba7b57897424516b0e8ca320f929730
Source dataset
uspto-grants-1988_07
Patent number
US04757078

Reaction notes

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