2,4-Difluorobenzaldehyde → 4-Fluoro-2-(methylthio)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4-difluorobenzaldehyde (3.0 g, 21.1 mmol, CAS RN 1550-35-2) in toluene (29 mL) was added sodium thiomethoxide (2.03 g, 28.9 mmol) and the resulting suspension was stirred at 80° C. for 7 hours. Heating was removed and stirring continued at room temperature for another 18 hours. The reaction mixture was treated with diethyl ether (50 mL) and water (15 mL) and the layers were separated. The aqueous layer was extracted twice with ethyl acetate (50 mL each). The organic layers were washed with saturated aqueous sodium hydrogencarbonate solution and with brine, dried over magnesium sulfate, filtered and evaporated. The residue was dissolved in 50 mL n-heptane and 50 mL diethyl ether and the clear solution was evaporated slowly until a turbid solution formed. The originally oily precipitation turned into a white solid which was filtered, washed with n-heptane and dried under high vacuum to give the compound as a colourless solid (1.35 g, 37%). MS (ESI+): m/z=170.0 ([M+H]+).

Provenance & Evidence