Dimethyl Disulfide → 2-Bromo-5-(methylthio)pyridine

Participants

Reaction Steps

To a solution of 2,5-dibromopyridine (23.4 g, 0.099 mol) in ether (500 mL), was added dropwise n-butyl lithium (n-BuLi) (1.52 M in n-hexane, 68 mL, 0.10 mmol) at −78° C. and the mixture was stirred for 1 hour at the temperature. Dimethyldisulfide (9.8 mL, 0.11 mol) was added slowly at −78° C. and the mixture was stirred for 1 hour at that temperature and further 1 hour at 0° C. The mixture was quenched with aqueous 1N hydrochloric acid (200 mL) and extracted with ether (100 mL×2), dried over MgSO4, and concentrated in vacuo to yield the title compound (18.9 g, 94%).

Provenance & Evidence