Cyclohexene oxide → 2-(4-Fluorophenyl)cyclohexanol

Participants

Reaction Conditions

Reaction Steps

To a cooled solution of 4-Fluorophenylmagnesium bromide (1.0M in THF, 4.94 mL, 4.94 mmol) in dry THF (10 mL) at −78° C. is added Copper (I) Bromide Dimethylsulfide complex (51 mg, 0.25 mmol) and the resulting mixture is stirred at −78° C. for 10 min, followed by the slow addition of a solution of 7-Oxa-bicyclo[4.1.0]heptane (500 μL, 4.94 mmol) in THF (2 mL). The reaction is warmed to 0° C. and is stirred for 2 hour. Then the reaction is quenched with saturated NH4Cl solution (20 mL). The resulting mixture is extracted with EtOAc (10 mL×3). The organic layers are combined, washed with brine (10 mL×1), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude is purified by silica flash column chromatography using EtOAc in Heptane (gradient from 0% to 35%) to give 700 mg of desired product.

Provenance & Evidence