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

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To a mixture of methyl 2-methylbenzoate (5.0 g, 0.033 mmol) and N-bromosuccinimide (5.9 g, 0.033 mmol) in CCl4 (50 mL) was added benzoyl peroxide (0.04 g, 0.00016 mmol). The mixture was heated to reflux for 1.5 h, cooled to room temperature, filtered through Celite, and concentrated to afford methyl 2-(bromomethyl)benzoate (7.2 g, ca. 94% mass recovery), which was contaminated with ca. 14% unreacted starting material and was used without purification.

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