Triphenylphosphine → [(3-Bromophenyl)methyl](triphenyl)phosphanium bromide

HRID 265868Notes

Reaction equation

HRID 265868 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CC#N>[Br-:1].[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][P+:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 699793-Bromobenzyl bromide

Product 1

HCID 19034144[(3-Bromophenyl)methyl](triphenyl)phosphanium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 3-bromobenzyl bromide (Aldrich) (5.1 g, 20.5 mmoles), triphenylphosphine (54 g, 0.20 moles), and CH3CN (100 mL) was refluxed for 20 hours. The cooled reaction mixture was then concentrated and the residue triturated with hexanes (10×) to remove excess triphenylphosphine. The remaining white solid was collected by filtration and then dried in vacuo to give 11-2 as a white solid.

Workup

  1. temperaturewas refluxed for 20 hours
  2. customThe cooled reaction mixture
  3. concentrationwas then concentrated
  4. customthe residue triturated with hexanes (10×)
  5. customto remove excess triphenylphosphine
  6. filtrationThe remaining white solid was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-f63b687e515343d29c82bad77df55f4d
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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