Benzoyl Peroxide → 6-Bromomethyl-nicotinic acid methyl ester

Participants

Reaction Steps

A mixture of methyl 6-methylnicotinate (2.00 g, 13.2 mmol) and CCl4 (88.2 mL) was treated with NBS (2.57 g, 14.5 μmmol) and benzoyl peroxide (320 mg, 1.32 mmol) and heated to a refluxing temperature overnight. The resulting brown suspension was concentrated and purified by MPLC (10-40% EtOAc in heptane to afford the requisite product as a yellow solid. 1H NMR (DMSO-d6, 600 MHz) δ 9.01 (dd, J=2.4, 0.8 Hz, 1H), 8.28 (dd, J=7.9, 2.1 Hz, 1H), 7.68 (dd, J=8.2, 0.9 Hz, 1H), 4.74 (s, 3H), 3.84 (s, 3H).

Provenance & Evidence