2-Bromo-3-methylpyridine

2-Bromo-3-methylpyridine is a diazido compound with a hydrogen bond. It reacts rapidly with copper chloride to form the coordination complex Cu(diazido)(Cl)2 and an organic product.

clear slightly yellow to light brown liquid

2-Bromo-3-methylpyridine is a halogenated pyridine analogue containing a bromine functional group. The substance is used as a reaction reagent and as a basic structural unit in organic synthesis for the preparation of other heterocyclic compounds.

2-Bromo-3-methylpyridine can be synthesized from 2,4-dibromopyridine by a cross coupling reaction with copper chloride and calcium carbonate in the presence of sodium potassium bicarbonate.

A solution of 2,3-dibromopyridine (0.10 M, 3.0 mL) in THF was stirred at T ℃. A solution of n-BuLi (0.40 M, 0.75 mL) in hexane was added dropwise to this solution at a regular pace for 1.0 min. After stirring for 10 min, iodomethane (0.60 M, 1.5 mL) was added dropwise to this mixture at a regular pace for 1.0 min. After stirring at T ℃ for 10 min, a cooling bath was removed. When the reaction mixture reached room temperature and was quenched with H2O, the yields of 2-bromo-3-methylpyridine (2) and 2-bromopyridine (3) and the conversion of 2,3-dibromopyridine (1) was analyzed by GC.