3-Bromopyridine → 3-(Trimethylstannyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-bromopyridine (1.58 g, 10 mmol) in anhydrous ethyl ether (100 mL) at −78° C. was added n-butyl lithium (1.6M in hexane, 7.5 mL) via a syringe, and the resulting solution was stirred at −78° C. for 10 minutes. Trimethyltin chloride (2.39 g, 12 mmol) was then added, and the mixture was stirred at −78° C. for 20 minutes, and then warmed to room temperature over 1 hour. The reaction mixture was diluted with hexanes (30 mL) and washed with water. The organic phase was dried and concentrated to give the crude product which was purified by vacuum distillation (125° C. at 15-20 mmHg) to give 3-trimethylstannyl pyridine (1.93 g, 80% yield).

Provenance & Evidence