Carbon Tetrachloride → Ethyl 2-(bromomethyl)pyridine-3-carboxylate--hydrogen chloride (1/1)

Participants

Reaction Steps

A mixture of ethyl 2-methylnicotinate (5.0 g, 30.3 mmol), N-bromosuccinimide (7.5 g, 42.1 mmol) and benzoyl peroxide (0.5 g) in carbon tetrachloride (100 ml) was heated under reflux for 6 hours, then allowed to cool. The resulting mixture was filtered, the filtered solid washed with carbon tetrachloride, and the combined filtrate washed with 4% sodium hydroxide solution, water and 2% hydrochloric acid, then dried over sodium sulphate. The solution was then treated with ethereal hydrochloric acid, and the resulting precipitate was filtered off, washed with ether and dried to afford the title compound as a pale yellow solid (4.5 g).

Provenance & Evidence