4-bromo-1-(chloromethyl)-2-methylbenzene synthesis

Yield:24078-15-7 86%

Reaction Conditions:

with methanesulfonyl chloride;triethylamine in dichloromethane at 20; for 16.5 h;Cooling with ice;Reagent/catalyst;

Steps:

2.B Alternative synthesis of 4-bromo-1-(chloromethyl)-2-methyl-benzene

Scheme 1, step B: 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).

References:

US2014/100179,2014,A1 Location in patent:Paragraph 0023; 0025