Triphenylphosphine → [(4-Fluoro-3-phenoxyphenyl)methyl](triphenyl)phosphanium bromide

HRID 1458393Notes

Reaction equation

HRID 1458393 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][Br:7])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Br-:7].[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][P+:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzene

Product 1

HCID 21703142[(4-Fluoro-3-phenoxyphenyl)methyl](triphenyl)phosphanium bromideYield 90.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4-fluoro-3-phenoxybenzyl bromide (42.17 g, 0.150 mol) in toluene is added to a solution of triphenyl phosphine (41.31 g, 0.158 mol) in toluene. The resultant reaction mixture is refluxed for one hour, cooled to room temperature, and filtered to obtain a solid. The solid is washed sequentially with toluene and hexanes, and dried in a dessicator at 60° C. to give the title product (73.7 g, 90.4%) which is identified by NMR spectral analyses.

Workup

  1. customThe resultant reaction mixture
  2. temperatureis refluxed for one hour
  3. filtrationfiltered
  4. customto obtain a solid
  5. washThe solid is washed sequentially with toluene and hexanes
  6. customdried in a dessicator at 60° C.

Sources & evidence

ORD record
ord-9fb659dd22e34a93b91741f9a77f58d8
Source dataset
uspto-grants-1998_12
Patent number
US05849958

Reaction notes

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