Cesium fluoride → 1-(Benzyloxy)-2-chloro-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene

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Reaction Steps

A solution of 4-benzyloxy-3-chlorobenzaldehyde (0.25 g, 2.0 mmol), 2,2,2-trifluoroethyltriphenylphosphonium trifluoromethanesulfonate (0.49 g, 1.0 mmol) and CsF (0.76 g, 5.0 mmol) in DMF (10 mL) was stirred at 25° C. for 16 h. The reaction was then diluted with ethyl acetate, washed with water and dried. Removal of the solvent gave a residue which was purified by preparative TLC to give 1-(3-chloro-4-benzyloxyphenyl)-3,3,3-trifluoropropene. This product (65 mg, 0.2 mmol) was dissolved in ethyl acetate (2 mL) and hydrogenated (1 atm) in the presence of 10% palladium on carbon for 1 hr. Removal of the catalyst and solvent give 2-chloro-4 (3,3,3-trifluoropropyl)phenol as an oil.

Provenance & Evidence