Water → 2-(4-Fluorophenyl)acetaldehyde

Participants

Reaction Steps

To a solution of 672 mg of o-iodoxybenzoic acid in methyl sulfoxide (5 mL) was added 250 μL of 2-(4-fluorophenyl)ethanol and stirring was continued for 3 h. Water (20 mL) was added and the reaction mixture filtered, the filtrate was extracted with ether (3×20 mL), washed with brine (10 mL), dried over magnesium sulfate, and concentrated to give 2-(4-fluorophenyl) ethanal as an unstable oil. The material was immediately dissolved in acetonitrile (3.5 mL) at 0° C. and 264 μL of bromotrimethylsilane and 142 μL of methyl sulfoxide were added. After stirring for 1 h, water (10 mL) was added and the reaction mixture was extracted with ether (3×20 mL), washed with brine (10 mL), dried over magnesium sulfate, and concentrated to give the title compound (220 mg) as an unstable oil which was used immediately without further purification.

Provenance & Evidence