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

Participants

Reaction Steps

2-Methylbenzoic acid methyl ester (582 mg, 3.88 mmol), N-bromosuccinimid (NBS) (759 mg, 4.26 mmol), and benzoyl peroxide (13 mg, 0.04 mmol) in CCl4 (10 mL) was stirred at reflux for 5 h. After cooling to room temperature, the reaction mixture was extracted with CH2Cl2 (×3). The extract was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (Hex/EtOAc=9:1) to give 2-(bromomethyl)benzoic acid methyl ester (Formula 5) as a white solid (850 mg, 96%). Rf=0.6 (Hex:EtOAc=9:1); 1H NMR (300 MHz, CDCl3): δ 7.97 (d, J=7.5 Hz, 1H), 7.48 (m, 2H), 7.38 (td, J=7.8 and 1.2 Hz, 1H), 4.96 (s, 2H), 3.95 (s, 3H). [lit.2 δ 7.97 (m, 1H), 7.40 (m, 3H), 4.96 (s, 2H), 3.95 (s, 3H).

Provenance & Evidence