Reaction #710468

Reaction equation

2-fluoro-5-methyl pyridine

N-bromosuccinimide

→

5-bromomethyl-2-fluoropyridine

Yield 35.1%

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Temperaturethe resulting mixture was heated
2. 2
   Temperaturerefluxed for 2.5 hours
3. 3
   Otherwas returned to room temperature
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   Otherpurified by silica gel column chromatography (hexane:ethyl acetate=19:1)

Procedure

500 mg (4.50 mmol) of 2-fluoro-5-methyl pyridine was dissolved in 50 ml of carbon tetrachloride, 1.20 g (6.76 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 2.5 hours. After the reaction was completed, the reaction solution was returned to room temperature, and the solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 300 mg (yield 35%) of 5-bromomethyl-2-fluoropyridine.

Source