Water → 1-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-cyano-4-fluorophenyl)-3-trifluoromethyl-5-bromomethyl pyrazole (2.5 g, 7.18 mmol) in DMSO (40 mL) was added copper (I) oxide (2.16 g, 15.08 mmol) and water (12 mL). The reaction mixture was stirred at 60° C. for 2 hours then cooled to RT and stirred at RT overnight. The next day, the mixture was filtered through celite, filter pad was washed with ethyl acetate (20 mL); the filtrate was partitioned between ethyl acetate (50 mL) and water (50 mL); organic phase was separated and washed with water (3×30 mL); dried over sodium sulfate; filtered, concentrated, flash chromatography (ethyl acetate:hexane, 1:6) to afford 1-(3-cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxymethyl pyrazole (1.7 g). CI mass spectrum m/z (rel. intensity) 286 (M+H, 100).

Provenance & Evidence