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

HRID 324534Notes

Reaction equation

HRID 324534 reaction equation
[C:1]1([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)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][Br:25]>CCOCC>[Br-:25].[F:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 680073-Fluorobenzyl bromide

Product 1

HCID 10527583Phosphonium, [(3-fluorophenyl)methyl]triphenyl-, bromideYield 107.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of triphenylphosphine (45.24 g, 0.12 mol) in 200 mL of ether was added 3-fluorobenzyl bromide (22.7 g, 0.12 mol). The resulting solution was allowed to stir at rt overnight. The white solid was collected by filtration and dried to give 58.0 g (85%) of the product as a white solid. mp 290-292° C. 1H NMR (CHCl3) 5.516 (d, J=14.7 Hz, 2 H), 6.725 (d, J=9.6 Hz, 1 H), 6.893 (m, 2 H), 7.084 (m, 2 H), 7.622-7.762 (m, 15 H).

Workup

  1. filtrationThe white solid was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-d51cc9a0904d452fb0c72051d624aba9
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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