Triphenylphosphine → (4-Fluoro-3-phenoxyphenyl)methyltriphenylphosphonium chloride

HRID 1588891Notes

Reaction equation

HRID 1588891 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Cl:9])=[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>O1CCCC1>[Cl-:9].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][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 135636494-(Chloromethyl)-1-fluoro-2-phenoxybenzene

Product 1

HCID 19754846(4-Fluoro-3-phenoxyphenyl)methyltriphenylphosphonium chlorideYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11.8 grams (0.05 mole) of 4-fluoro-3-phenoxyphenylmethyl chloride (prepared in Example 2, Step B) and 13.1 grams (0.05 mole) of triphenylphosphine in 150 mL of dry tetrahydrofuran was stirred for about 60 hours. After this time the reaction mixture was concentrated under reduced pressure to a solid residue. The solid was stirred with diethyl ether and was collected by filtration, yielding 15 grams of (4-fluoro-3-phenoxyphenyl)methyltriphenylphosphonium chloride.

Workup

  1. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a solid residue
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b9b22a9537e44d80ab852cb5ff771a19
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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