N-bromobutanimide → Methyl 2-(4-(bromomethyl)phenyl)-2-methylpropanoate

Participants

Reaction Steps

To a refluxing solution of 2-Methyl-2-p-tolyl-propionic acid methyl ester (892 mg, 4.64 mmol) and N-bromosuccinimide (826 mg, 4.64 mmol) in CCl4 (120 mL) is added 2,2′-Azobisisobutyronitrile (12 mg, 0.073 mmol). After 5 h, the reaction is concentrated and the residue is chromatographed (SiO2 120 g, 5% to 20% EtOAc/Hex) to yield the title compound (906 mg, 72%) 1H NMR (400 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 4.48 (s, 2H), 3.65 (s, 3H), 1.57 (s, 6H).

Provenance & Evidence