N-bromobutanimide → Tert-butyl 4-(bromomethyl)-3-methoxybenzoate

Participants

Reaction Steps

A suspension of t-butyl 3-methoxy-4-methylbenzoate (8.9 g), N-bromosuccinimide (8.57 g), and benzoyl peroxide (0.1 g) in carbon tetrachloride (150 ml) was heated to reflux and irradiated with a sun lamp for 1 hour. After cooling to room temperature, the suspension was filtered; and the filtrate was evaporated. The residue was purified by flash chromatography on silica gel (700 ml), eluting with 5:95 ethyl acetate:hexane to give t-butyl 4-bromomethyl-3-methoxybenzoate (11.52 g, 95%) as a pale yellow oil; NMR (80 MHz, CDCl3) 1.5[s, 9H, C(CH3)3 ], 3.9(s, 3H, OCH3), 4.5(s, 2H, CH2Br), 7.15(d, 1H), 7.4(m, 2H).

Provenance & Evidence