N-bromobutanimide → Methyl 3-bromo-2-(bromomethyl)benzoate

Participants

Reaction Steps

Methyl 3-bromo-2-methylbenzoate (7.45 g, 32.5 mmol) was dissolved in CCl4 (94 ml) and N-bromosuccinimide (6.67 g, 37.5 mmol) and benzoyl peroxide (0.38 g, 1.6 mmol) were added. The reaction was heated to 75 C-85 C, stirred for 3 hours and 45 minutes, cooled to room temperature, and filtered. The filtrate was concentrated and purified on SiO2 (Biotage instrument; 0%->20% EtOAc/hexanes) to give methyl 3-bromo-2-(bromomethyl)benzoate (10.07 g, 100%).

Provenance & Evidence