Toluene → Pentafluorobenzyltriphenylphosphonium bromide

HRID 1249649Notes

Reaction equation

HRID 1249649 reaction equation
C1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)C=CC=CC=1.[F:20][C:21]1[C:26](C[Br:28])=[C:25]([F:29])[C:24]([F:30])=[C:23]([F:31])[C:22]=1[F:32].[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[Br-:28].[F:29][C:25]1[C:26]([P+:7]([CH2:39][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:21]([F:20])[C:22]([F:32])=[C:23]([F:31])[C:24]=1[F:30]

Participants

4

Reactant 3

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 74484Pentafluorobenzyl bromide

Product 1

HCID 87730649Pentafluorobenzyltriphenylphosphonium bromideYield 90%

Procedure

A five-liter, three-necked flask equipped with a mechanical stirrer, reflux condenser, and thermometer was charged with toluene (3.3 liters), triphenylphosphine (686 g, 2.62 mole), and pentafluorobenzyl bromide (343 g, 1.31 mole). The contents were stirred and heated slowly to reflux. A white precipitate formed as the reaction progressed. At the completion of the reaction the flask was cooled to ambient temperature and the solid product was filtered and washed with hot toluene (2.6 liters). These solids were dried in a vacuum desiccator to give a 90% yield of pentafluorobenzyltriphenylphosphonium bromide.

Workup

  1. customA five-liter, three-necked flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureheated slowly
  4. temperatureto reflux
  5. customA white precipitate formed as the reaction
  6. customAt the completion of the reaction the flask
  7. filtrationthe solid product was filtered
  8. washwashed with hot toluene (2.6 liters)
  9. customThese solids were dried in a vacuum desiccator

Sources & evidence

ORD record
ord-17688f8e310142d09b1573f1989d69f4
Source dataset
uspto-grants-1986_12
Patent number
US04633020

Reaction notes

Loading…