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

HRID 1110411Notes

Reaction equation

HRID 1110411 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 and 13.1 grams (0.05 mole) of triphenylphosphine in 150 mL of dry tetrahydrofuran was stirred for 72 hours. After this time the reaction mixture was concentrated under reduced pressure to a residual solid. The residue was stirred with diethyl ether and filtered to collect the solid. The solid was washed repeatedly with diethyl ether and dried yielding 15.0 grams of 4-fluoro-3-phenoxyphenylmethyltriphenylphosphonium chloride.

Workup

  1. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residual solid
  2. filtrationfiltered
  3. customto collect the solid
  4. washThe solid was washed repeatedly with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-abab2ad225ab43298b07b82f686be21a
Source dataset
uspto-grants-1990_12
Patent number
US04975451

Reaction notes

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