2,2,2,4'-Tetrafluoroacetophenone → 1-Fluoro-4-[2-phenyl-1-(trifluoromethyl)ethenyl]benzene

HRID 1382629Notes

Reaction equation

HRID 1382629 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[O-][CH2:15][CH3:16].[Na+]>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>[C:15]1([CH:16]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 2723922Sodium ethoxide

Product 1

HCID 572512121-Fluoro-4-[2-phenyl-1-(trifluoromethyl)ethenyl]benzeneYield 91%

Reagents, catalysts & solvents 2

HCID 70671Benzyltriphenylphosphonium chlorideCatalystHCID 702EthanolSolvent

Procedure

4'-Fluoro-2,2,2-trifluoroacetophenone (F. E. Herkes et al.: J. Org. Chem. 32, 1311-18 (1967)) is reacted with benzyl-triphenyl-phosphonium chloride in the presence of an ethanol solution of sodium ethoxide. 1-Phenyl-3,3,3-trifluoro-2-(4-fluorophenyl)-propene is obtained with a yield of 91%; b.p.: 110°-114° C./0.2 mm Hg, m.p.: 43°-45° C.

Sources & evidence

ORD record
ord-a832ee8a18f0423baefa1449b5fb07c3
Source dataset
uspto-grants-1989_02
Patent number
US04806685

Reaction notes

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