反应详情

A solution of tetra-n-butylammonium fluoride (6.12 g, 19 mmol) in tetrahydrofuran (20 mL) was added dropwise to a solution of 4-bromo-3-[2-(tert-butyl-dimethyl-silanyloxy)-3-chloro-benzylsulfanyl]-5-methyl-benzoic acid methyl ester (5 g, 96.9 mmol) in tetrahydrofuran (50 mL) under nitrogen at 5° C. and stirring was continued for 0.5 h. It was concentrated, treated with chilled water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, ethyl acetate/pet ether) to obtain the title compound as a white solid. Yield: 3.0 g, (95%); 1H NMR (CDCl3): δ 2.42 (s, 3H, CH3), 3.88 (s, 3H, OCH3), 4.34 (s, 2H, CH2), 6.81 (t, 1H, Ar), 7.29 (t, 2H, Ar), 7.7 (s, 2H, Ar); MS: m/e (EI+) 401 (M+).

1. concentrationIt was concentrated
2. additiontreated with chilled water
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with water, brine
5. customdried
6. concentrationconcentrated
7. custompurified