Reaction #710467

Reaction equation

2-chloro-3-fluoro-5-methyl pyridine

N-bromosuccinimide

→

5-(bromomethyl)-2-chloro-3-fluoropyridine

Yield 51.0%

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Temperaturethe resulting mixture was heated
2. 2
   Temperaturerefluxed overnight
3. 3
   Otherwas returned to room temperature
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   Otherpurified by silica gel column chromatography (hexane:ethyl acetate=19:1)

Procedure

4.00 g (27.6 mmol) of 2-chloro-3-fluoro-5-methyl pyridine was dissolved in 80 ml of carbon tetrachloride, 7.37 g (41.4 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed overnight. After the reaction was completed, the reaction solution was returned to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 3.06 g (yield 51%) of 5-(bromomethyl)-2-chloro-3-fluoropyridine.

Source