Benzoyl Peroxide → Methyl 4-(bromomethyl)benzoate

참여 물질

반응 단계

Methyl 4-methylbenzoate 3 (2.9 g, 19.3 mmol) was dissolved in tetrachloromethane (CCl4, 20 mL) at room temperature. N-bromosuccinimide (NBS, 3.5 g, 19.0 mmol) and benzoyl peroxide (BPO, 0.26 g, 1.9 mmol) was added. The resulting mixture was stirred at reflux for 5 hr, then cooled to room temperature, washed with saturated sodium bicarbonate solution and brine, dried with anhydrous sodium sulfate and condensed under vacuum. The residue was purified by silica gel chromatography (petrol ether:ethyl acetate=50:1 to 10:1) to get a white solid of methyl 4-(bromomethyl)benzoate (4.3 g, 97%), LC-MS (ESI) m/z 230 [M+1]+.

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