Reaction #710470

Reaction equation

2-bromo-5-methylpyridine

N-bromosuccinimide

→

2-bromo-5-bromomethylpyridine

Yield 20.0%

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Temperaturethe resulting mixture was heated
2. 2
   Temperaturerefluxed for 19 hours
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

500 mg (2.92 mmol) of 2-bromo-5-methylpyridine was dissolved in 15 ml of carbon tetrachloride, 623 mg (3.50 mmol) of N-bromosuccinimide and 10 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 19 hours. 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 143 mg (yield 20%) of 2-bromo-5-bromomethylpyridine.

Source