Acetone → 1-(3-Bromophenyl)-1-fluoro-2-hydroxy-2-methylpropane-1-sulfonamide

Participants

Reaction Steps

Under inert gas, 310 mg of C-(3-bromophenyl)-N,N-bis(2,4-dimethoxybenzyl)-C-fluoromethanesulfonamide were initially charged in 10 ml of THF, and then, at a temperature of −78° C., 0.68 ml of a 1.6 N methyllithium solution in diethyl ether were added dropwise and the mixture was stirred at constant temperature for 10 minutes. Subsequently, 0.25 ml of acetone were added. After stirring for 10 minutes, the reaction solution was admixed with 0.10 ml of trifluoroacetic acid, and the reaction mixture was allowed to come to room temperature and concentrated by rotary evaporation. The residue was dissolved in 10 ml of dichloromethane, 1.5 ml of trifluoroacetic acid were added and the mixture was stirred at room temperature for 20 minutes. The reaction solution was freed of the solvent and the crude product was purified by means of normal phase chromatography using a Flashmaster with a dichloromethane/methanol gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (77.9 mg) with a molecular weight of 326.2 g/mol (C10H13BrFNO3S); MS (ESI): m/e=345 (M+H2O+H+).

Provenance & Evidence