Methyl o-toluate → Methyl 2-(bromomethyl)benzoate

Participants

Reaction Steps

To a solution of methyl-2-methylbenzoate (3.00 g, 20.0 mmol) in carbon tetrachloride (15 mL) was added N-Bromosuccinimide (3.55 g, 20.00 mmol). The reaction was allowed to stirr at reflux for 3 h. The mixture was cooled and then partioned between 1:1 ethyl acetate/hexane and the combine organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent under reduced pressure afforded the title compound as a yellowish liquid (4.70 g, quantitative yield). 1H NMR (400 MHz, CDCl3) δ 7.98 (d, 1H), 7.54-7.35 (mm, 3H), 4.98 (s, 2H), 3.98 (s, 3H).

Provenance & Evidence