Water → 4-bromo-2-hydroxy-N(3-trifluoromethylphenyl)butanamide

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Reaction Steps

Boron tribromide (11.0 ml, 1.0M solution in dichloromethane) was added dropwise to a stirred solution of 3-hydroxytetrahydrofuran-2-one (1.0 g) and 3-trifluoromethylphenylaniline (1.58 g) in 1,2-dichloroethane (20 ml). The mixture was stirred overnight at room temperature, poured on to water and extracted with dichloromethane. The extracts were washed with hydrochloric acid (2M) and brine, dried over magnesium sulphate, and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ethanol (49:1) as eluant, to give the title compound (0.74 g, m.p. 67°-69° C.). NMR (CDCl3): δ 2.3(1H,m); 2.6(1H,m); 3.5(1H,bs); 3.6(2H,dd); 4.5(1H,dd); 7.4(2H,m); 7.7 (1H,d); 7.9(1H,s); 8.7(1H,bs). MS: M+ 325, 327.

Provenance & Evidence