Carbon tetrabromide → 3-Tert-butyldimethylsilyloxymethylbenzyl bromide

Participants

Reaction Steps

To a mixture of [3-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]methanol (J. Med. Chem. 1996, 25, 4871., 4.39 g, 17 mmol) and carbon tetrabromide (8.95 g, 27 mmol) in tetrahydrofuran (60 mL) was added triphenylphosphine (6.82 g, 26 mmol) in two portions at 0° C. and the mixture was stirred for 3 h at room temperature. The mixture was neutralized with aqueous sodium hydrogen carbonate and extracted with dichloromethane. The organic layer was concentrated. The residue was taken up in hexane and the resulting mixture was filtered, and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane/dichloromethane (10/1) to afford 760 mg (14%) of the title compound as a colorless oil:

Provenance & Evidence