反应详情

To a solution of 4-chloro-N-{2-[2-(3-methoxyphenyl)-1-pyrrolidinyl]ethyl}benzamide (0.58 g) in chloroform (30 ml) was added boron tribromide (99.0%, 0.61 ml) at -10° C., under nitrogen. The cooling bath was removed after 15 mins, and the reaction mixture was allowed to warm to ambient temperature. Crushed ice was added followed by 5:1-chloroform/2-propanol. The layers were separated, and the aqueous phase was extracted with 5:1 chloroform/2-propanol (2 times). The combined organic extracts were washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, 30% ethyl acetate/dichloromethane). The appropriate fractions were collected and concentrated to afford 0.29 g (52%) of 4-chloro-N-{2-[2-(3-hydroxyphenyl)-1-pyrrolidinyl]ethyl}benzamide.

1. customThe cooling bath was removed after 15 mins
2. additionCrushed ice was added
3. customThe layers were separated
4. extractionthe aqueous phase was extracted with 5:1 chloroform/2-propanol (2 times)
5. washThe combined organic extracts were washed with saturated sodium bicarbonate
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationthe filtrate was concentrated
9. customThe residue was purified by flash column chromatography (silica gel, 30% ethyl acetate/dichloromethane)
10. customThe appropriate fractions were collected
11. concentrationconcentrated