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.
