Triphenylphosphine → 2-Cyanobenzyltriphenylphosphonium bromide

HRID 1034305Notes

Reaction equation

HRID 1034305 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Br:6])#[N:2].[CH:11]1[CH:16]=[CH:15][C:14]([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:13][CH:12]=1>CC#N>[Br-:6].[C:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][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:14]1[CH:13]=[CH:12][CH:11]=[CH:16][CH:15]=1)#[N:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 105999462-Cyanobenzyltriphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-cyanobenzyl bromide (Aldrich; 2.0 g) and Ph3P (3.2 g) in 30 mL CH3CN were stirred for 3 days under nitrogen. The solution was concentrated to 15 mL, Et2O added, and the precipitate collected to provide 2-cyanobenzyltriphenylphosphonium bromide as a white solid.

Workup

  1. concentrationThe solution was concentrated to 15 mL, Et2O
  2. additionadded
  3. customthe precipitate collected

Sources & evidence

ORD record
ord-e94e60744e2e4045a97502f3ec0dff82
Source dataset
uspto-grants-1994_05
Patent number
US05314900

Reaction notes

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