Water → 4-Bromo-1-(chloromethyl)-2-methylbenzene

Participants

Reaction Steps

Methanesulfonyl chloride (171 mL, 2.11 mol) is added over 30 minutes to a mixture of (4-bromo-2-methyl-phenyl)methanol (250 g, 1.24 mol) and triethylamine (304 mL; 2.11 mol) in dichloromethane (2500 mL) cooled in ice/water. The mixture is allowed to warm to ambient temperature and is stirred for 16 hours. Water (5000 mL) is added and the product is extracted with dichloromethane (2×7000 mL). The combined organic layers are washed with saturated aqueous NaCl solution (5000 mL) and dried over Na2SO4. Filtration and concentration under reduced pressure provides a residue which is passed through a silica pad (eluting with hexane and ethyl acetate) to provide the title compound (234 g; 86% yield).

Provenance & Evidence