Triphenylphosphine → Phosphonium, nonyltriphenyl-, bromide (1:1)

HRID 365039Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A magnetically stirred suspension of 1-bromononane (Aldrich, 40 g, 0.1931M) and triphenylphosphine (101.3 g, 0.3862 mole) was heated at 100° C. (oil bath) for 2 hours. The resulting homogeneous solution was then cooled and triturated with ether (8X) to remove most of the unreacted triphenylphosphine. A viscous gum was obtained which was dissolved in CH2Cl2 and concentrated in vacuo to give the title phosphonium salt as a light yellow, extremely hygroscopic foam weighing 85 g (80.1%). TLC, neat CH2Cl2, Rf =0.78, PMA.

Workup

temperatureThe resulting homogeneous solution was then cooled
customtriturated with ether (8X)
customto remove most of the unreacted triphenylphosphine
customA viscous gum was obtained which
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-271c3869a1e246b8ab90e30c700e5837
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04607053

Reaction notes

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