Acetic Acid → 1-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-propan-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of freshly prepared 1-methanesulfonyl-4-(2-nitro-propenyl)-2-trifluoromethyl-benzene (59b) (14 g, 45 mmol) in acetic acid (100 ml) is added slowly to a stirred slurry of Iron powder (27.6 g, 495 mmol) in acetic acid (100 ml) at 60° C. The reaction is then stirred at 100° C. for 2 hours then allowed to cool and poured onto ice-water (300 ml). After filtration through celite, washing with dichloromethane (500 ml), the organic extract is separated and washed with water (3×300 ml) followed by brine (500 ml). The organic extract is dried (MgSO4) and concentrated to give a red oil. Chromatography on silica, eluting with ethyl acetate-hexane, affords the titled compound as a white solid.

Provenance & Evidence