N-bromosuccinimide (178 g, 1.00 mmol) was slowly added to a solution of toluene (1.0 L) containing 3,5-dimethylphenol (122 g, 1.00 mol) under ice bath cooling conditions. The reaction mixture was then gradually warmed to room temperature and stirred continuously for 2 hours. Upon completion of the reaction, the mixture was concentrated by distillation under reduced pressure and the resulting residue was suspended in hexane (400 mL) and filtered to remove insoluble matter. The filtrate was further concentrated and the resulting crude product was purified by silica gel column chromatography (eluent: hexane-ethyl acetate, 9:1) to afford 61.6 g of the target product, 2-bromo-3,5-dimethylphenol, in 31% yield. The structure of the product was confirmed by 1H-NMR (CDCl3): δ 2.23 (3H, s), 2.34 (3H, s), 5.51 (1H, s), 6.60-6.64 (1H, m), 6.66-6.69 (1H, m).
