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

Participants

Reaction Steps

Add thionyl chloride (14.31 mL, 0.2 mol) to a solution of (4-bromo-2-methyl-phenyl)methanol (32.9 g, 0.16 mol) in dichloromethane (200 mL) and dimethylformamide (0.025 mol, 2.0 mL) at 0° C. After 1 hour at room temperature, pour the mixture into ice-water (100 g), extract with dichloromethane (300 mL), wash extract with 5% aq. sodium bicarbonate (30 mL) and brine (200 mL), dry over sodium sulfate, filter, and concentrate under reduced pressure to provide the crude title compound as a white solid (35.0 g, 0.16 mol). The material is used in the next step without further purification. 1H NMR (CDCl3): δ 2.38 (s, 3H), 4.52 (s, 2H), 7.13-7.35 (m, 3H).

Provenance & Evidence