Реакция #169642

Уравнение реакции

benzoyl peroxide

2-fluoro-4-methylpyridine

N-bromosuccinimide

benzoyl peroxide

→

4-(bromomethyl)-2-fluoropyridine

Растворители

dichloromethane

carbon tetrachloride

Условия реакции

Обработка

1. 1
   Промывкаwashed 3× with water
2. 2
   Сушкаdried over sodium sulfate
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   ДругоеThe residue was purified via silica gel chromatography
6. 6
   Промывкаeluting with 0-10% ethyl acetate in hexanes

Методика

To a solution of 2-fluoro-4-methylpyridine (0.510 g, 4.59 mmol) in 20 mL of carbon tetrachloride was added N-bromosuccinimide (0.899 g, 5.05 mmol) and benzoyl peroxide (0.148 g, 0.459 mmol). The mixture was heated to 90° C. for 1 h, and then additional benzoyl peroxide (0.074 g, 0.23 mmol) was added. After 20 h, the reaction was diluted with dichloromethane, washed 3× with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-10% ethyl acetate in hexanes to provide the 4-(bromomethyl)-2-fluoropyridine that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 191.9 (81Br) for [M+H]+.

Источник