Imidazole → (2-Bromoethoxy)(tert-butyl)diphenylsilane

Participants

Reaction Steps

To a stirred solution of 2-bromoethanol (25 g, 200 mmol) and imidazole (41 g, 600 mmol) in dichloromethane (300 mL) was added tert-butyldiphenylchlorosilane (55 mL, 210 mmol) at room temperature and the mixture was stirred for 24 h. The resulting mixture was poured into ice-water, extracted with dichloromethane (2×250 mL), washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, hexanes) afforded (2-bromo-ethoxy)-tert-butyl-diphenyl-silane (60 g, 83%) as a colorless oil.

Provenance & Evidence