Dimethyl Sulfoxide → 1-(1-Fluorocyclopropyl)-3-(4-fluorophenyl)-3-methylbutan-1-one

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Reaction Steps

2.2 mL of a 2 M solution of oxalyl chloride in dichloromethane was diluted with 2.5 mL of dichloromethane and cooled on dry ice/acetone bath. To this solution was added a dropwise a solution of 0.7 mL of DMSO in 2.5 mL of dichloromethane. After 10 minutes, a solution of the above crude 1-(1-fluorocyclopropyl)-3-(4-fluorophenyl)-3-methylbutan-1-ol (0.72 g, 3.0 mmol) in 2 mL of dichloromethane was added and the mixture was stirred for 15 minutes. 4 mL of triethylamine was added, the cooling bath was removed, the mixture was allowed to warm to room temperature and was then quenched with water and diluted with hexanes. The organic layer was separated, washed with water, dried, filtered, and concentrated in vacuo. The residue was purified by chromatography over silica gel (eluent: hexanes to hexanes-dichloromethane (4:1) gradient) to give 0.37 g of the title product as an oil.

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