Water → (R)-N-[4-(4-Bromophenylsulphonyl)-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

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Reaction Steps

Oxalyl chloride (0.029 ml) was added to a stirred suspension of (R)-(+)-2-hydroxy-2-methyl-3,3,3-trifluoropropanoic acid (Method 9) (0.047 g) in dichloromethane (3 ml) containing DMF (1 drop). The mixture was stirred at ambient temperature for 30 minutes and was then added to a solution of 4-(4-bromophenylsulphonyl)-2-chloroaniline (Method 12) (0.104 g) in dichloromethane (3 ml) and stirred a further 1 hour. Water (10 ml) was added and the mixture was extracted with dichloromethane (3×20 ml). The organic extracts were combined, washed with brine then dried. Volatile material was removed by evaporation and the residue was purified by flash chromatography on silica gel eluting with 1% methanol/dichloromethane to give the title compound (0.049 g) as a foam. NMR (CDCl3): 1.78 (s, 3H), 7.65 (d, 2H), 7.8 (m, 3H), 8.0 (s, 1H), 8.6 (d, 2H), 9.3 (s, 1H);MS: 485 (M+).

Provenance & Evidence