Carbon tetrabromide → [2-(Bromomethyl)phenoxy](tert-butyl)dimethylsilane

Participants

Reaction Steps

[2-(Bromomethyl)phenoxy](tert-butyl)dimethylsilane was prepared according to the literature procedure (J. Chem. Soc. Perkin Trans.1; 1988; 1417). To a solution of (2-([tert-butyl(dimethyl)silyl]oxy}phenyl)methanol (9.9 g/41.5 mmol) in acetonitrile (200 ml) was added carbon tetrabromide (14.5 g/43.6 mmol), triphenylphosphine (11.4 g/43.6 mmol) successively at 0° C., and then the resulting solution was stirred at room temperature for 16 hours. The solvent was evaporated. The residue was purified by column chromatography (SiO2, 200-350 mesh/hexane:ethyl acetate=100:1-20:1-10:1) to afford a colorless oil (12.0 g/96%).

Provenance & Evidence