2,2,2-Trifluoro-4'-methoxyacetophenone → 3,3,3-Trifluoro-1-(4-fluorophenyl)-2-(4-methoxyphenyl)-propene

HRID 1382635Notes

Reaction equation

HRID 1382635 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)C=CC=CC=1.[O-]CC.[Na+]>C(O)C>[F:11][C:10]([F:13])([F:12])[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[CH:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1365552,2,2-Trifluoro-4'-methoxyacetophenoneHCID 2723922Sodium ethoxideHCID 2733554(4-Fluorobenzyl)triphenylphosphonium chloride

Product 1

HCID 572170653,3,3-Trifluoro-1-(4-fluorophenyl)-2-(4-methoxyphenyl)-propeneYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4'-Methoxy-2,2,2-trifluoroacetophenone (R. Fuchs: J. Org. Chem. 22, 993-994 (1957)) is reacted with triphenyl(4-fluorobenzyl)-phosphonium chloride (see Example 18) in ethanol in the presence of sodium ethoxide. 3,3,3-Trifluoro-1-(4-fluorophenyl)-2-(4-methoxyphenyl)-propene is obtained with a yield of 87%; b.p.: 138°-142° C./0.5 mm Hg.

Sources & evidence

ORD record
ord-277848f9c6df4b28b5bbffe0f636b73f
Source dataset
uspto-grants-1989_02
Patent number
US04806685

Reaction notes

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