Carbon tetrabromide → tert-Butyl 3-(bromomethyl)phenylcarbamate

Participants

Reaction Steps

To a solution of tert-butyl[3-(hydroxymethyl)phenyl]carbamate (0.90 g, 4.0 mmol) in dichloromethane (15 mL) cooled at 0° C. was added triphenylphosphine (1.59 g, 6.05 mmol) and carbon tetrabromide (2.01 g, 6.05 mmol) and the reaction was stirred at rt overnight. The reaction was quenched with water and extracted with DCM (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 20% EtOAc/hexanes) to afford tert-butyl[3-(bromomethyl)phenyl]carbamate (0.82 g, 70%). LC-MS: (FA) ES+ 271.

Provenance & Evidence