Triphenylphosphine → (m-Trimethylsilylbenzyl)phosphonium bromide

HRID 466325Notes

Reaction equation

HRID 466325 reaction equation
[CH3:1][Si:2]([CH3:12])([CH3:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][Br:7].C1([P:19](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[Br-:7].[CH3:1][Si:2]([CH3:12])([CH3:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][PH3+:19]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 12583977(3-(Bromomethyl)phenyl)trimethylsilane

Product 1

HCID 19591670(m-Trimethylsilylbenzyl)phosphonium bromideYield 163.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 730 mg (3.00 mmol) of m-trimethylsilylbenzyl bromide and 1.18 g (4.50 mmol) of triphenylphosphine in 10 ml of dry toluene was refluxed for 4.5 hours in an atmosphere of argon (125°-135° C. by oil bath). The precipitate was collected by filtration, and washed with toluene to give 1.361 g of white crystals, which were dried in vacuo (yield 90%).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with toluene

Sources & evidence

ORD record
ord-c91c48f3da20472da83a582e2ee2f0f4
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Reaction notes

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