Tributyltin Chloride → 2-Methyl-5-(tributylstannyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A solution containing 5-bromo-2-methylpyridine (1.2 g, 6.98 mmol) in ether (14 mL) at −78° C. was treated with n-butyllithium (5.2 mL, 1.6 M in hexanes) dropwise, stirred at −78° C. for 1 hour, treated with tributyltin chloride (2.25 mL, 8.30 mmol), stirred at −78° C. for 0.5 hours, and then at 0° C. for 0.5 hours. The reaction was quenched with saturated ammonium chloride solution and the reaction was partitioned between ether and water, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound (2.97 g), which was used without further purification.

Provenance & Evidence