Carbon tetrabromide → 1-(Bromomethyl)-2-methoxybenzene

Participants

Reaction Steps

To a 100-mL round-bottomed flask was added 2-methoxybenzyl alcohol (1.33 mL, 9.99 mmol, Aldrich, St. Louis, Mo.), triphenylphosphine (2.62 g, 9.99 mmol, Aldrich, St. Louis, Mo.) and carbon tetrabromide (0.969 mL, 9.99 mmol, Aldrich, St. Louis, Mo.) in dichloromethane (20 mL). The reaction mixture was stirred at room temperature for 4 h and then the solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 10% EtOAc in hexanes to give 1-(bromomethyl)-2-methoxybenzene (1.78 g) as a white solid.

Provenance & Evidence