2-Bromopyridine → 2-(Tributylstannyl)pyridine

Participants

Reaction Conditions

Reaction Steps

n-BuLi (200 mL, 0.5 mol) was added dropwise to 2-bromopyridine (79 g, 0.5 mol) under N2 with continuous stirring at −78° C. This solution was stirred at −78° C. for 1 h and (Bu)3SnCl (178.8 g, 0.55 mol) was added dropwise to the reaction solution. After addition, the reaction solution was stirred at −78° C. for 1 h and room temperature for 1 h. TLC (petroleum:EtOAc=10:1) indicated the reaction was complete. The reaction solution was quenched with sat. NH4Cl and extracted with EtOAc (350 mL×3). The combined extracts were washed with water, dried over Na2SO4, concentrated and purified by chromatography, eluted with (petroleum:EtOAc=10:1) to give title compound (110 g, 60%) as a yellow liquid.

Provenance & Evidence