反应详情

To a solution of 5-Bromo-2-chlorobenzylalcohol (5.15 g) in N,N-dimethylformamide (50 ml) was added diisopropylethylamine (19.8 ml) and tert-butyldiphenylchlorosilane (11.9 ml), and the mixture was stirred at room temperature for 2 days. Under ice-cooling, to the mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with successively with 0.4 M aqueous hydrochloric acid solution (twice), water, a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by an aminosilane-treated silica gel column chromatography (hexane) to give 5-bromo-2-chloro-1-(tert-butyldiphenylsiloxymethyl)benzene 77 (10.79 g) as colorless oil. APCI-Mass m/Z 476/478 (M+NH4).

1. temperatureUnder ice-cooling, to the mixture
2. extractionthe mixture was extracted with ethyl acetate
3. washThe extract was washed with successively with 0.4 M aqueous hydrochloric acid solution (twice), water
4. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine, and dried over magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by an aminosilane-
7. additiontreated silica gel column chromatography (hexane)