2-Bromopyridine → Pyridine, 2-(trimethylstannyl)-

Participants

Reaction Steps

A solution of 15.7 mL of 1.6M n-butyllithium (25.1 mmol) in anhydrous ether (25 mL) was stirred under Ar at -78° C. and to this was added a solution of 2-bromopyridine (3.97 g, 25.1 mmol) in anhydrous ether (12.5 mL). The resulting orange solution was stirred for 2 h, and trimethyltin chloride in THF (26.0 mmol, 26 and, 1.0M) added over 30 min. The reaction was stirred for 1 h at -78° C. then warmed to room temperature over 1 h, filtered and the filtrate evaporated. Distillation afforded 3.1 g (51%) of the title compound as a colorless liquid which solidified in the receiver flask. B.p. 65° C./2 mm Hg; Literature B.p. 75° C./4 mm Hg.

Provenance & Evidence