反应详情

A mixture of (3S)-4-(4-fluorophenoxy)-3-hydroxy-1-butyne (2.5 g, 14 mmol), N-bromosuccinimide (NBS) (2.74 g, 15.4 mmol) and AgNO3 (0.12 g, 0.7 mmol) in acetone (70 mL) was stirred at ambient temperature. The pale solution became cloudy over 30 minutes. The mixture was concentrated under vacuum and the resulting residue was filtered through a plug of silica gel (1×5 cm) eluted with 1:4 ethyl acetate:hexane to obtain (3S)-1-bromo-4-(4-fluorophenoxy)-3-hydroxy-1-butyne, a compound of formula (CC), as a pale yellow oil containing some ethyl acetate, 4.75 g (quant.); 1H NMR (CDCl3) δ 3.95-4.15 (m, 2H), 4.75 (m, 1H), 6.86 (m, 2H), 6.97 (m, 2H) ppm.

1. concentrationThe mixture was concentrated under vacuum
2. filtrationthe resulting residue was filtered through a plug of silica gel (1×5 cm)
3. washeluted with 1:4 ethyl acetate