Triphenylphosphine → Phosphonium, [(3-fluorophenyl)methyl]triphenyl-, bromide

HRID 928081Notes

Reaction equation

HRID 928081 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][Br:6].[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>C1(C)C=CC=CC=1>[Br-:6].[F: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 680073-Fluorobenzyl bromide

Product 1

HCID 10527583Phosphonium, [(3-fluorophenyl)methyl]triphenyl-, bromideYield 84.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-fluorobenzyl bromide (5 g) and triphenyl phosphine (6.94 g) in toluene (50 mL) was heated at reflux for 3 hours. After cooling, the solid was collected by filtration, washed with toluene and dried under vacuum at 50° C. to give (3-fluorobenzyl)triphenylphosphonium bromide (10.1 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe solid was collected by filtration
  5. washwashed with toluene
  6. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-3d2b5c4e47394095b44286b0654be188
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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