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

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).

1. temperaturewas heated
2. temperatureunder reflux for 6 hours
3. temperatureto cool
4. filtrationThe resulting mixture was filtered
5. washthe filtered solid washed with carbon tetrachloride
6. washthe combined filtrate washed with 4% sodium hydroxide solution, water and 2% hydrochloric acid
7. dry with materialdried over sodium sulphate
8. additionThe solution was then treated with ethereal hydrochloric acid
9. filtrationthe resulting precipitate was filtered off
10. washwashed with ether
11. customdried

ORD record

ord-7ba493fbd2a4497ea6459bdf9bba5351

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06933312B2