2-Bromopyridine → 2-(Tributylstannyl)pyridine

Participants

Reaction Steps

To a solution of 10.0 g of 2-bromo-pyridine under nitrogen in 100 ml of tetrahydrofuran while cooling in a dry ice-acetone bath is added dropwise 47.0 ml of a 1.6M solution of butyl lithium via syringe. Stirring is continued for 1 hour. To the reaction mixture is added dropwise 24.7 g of tributyltin chloride in 30 ml of tetrahydrofuran and stirred 1 additional hour. The reaction mixture is quenched with 20 ml of water and 100 ml additional water is added. After stirring for 20 minutes the reaction mixture is extracted with chloroform (3×100 ml). The organic layer is filtered through diatomaceous earth and the filtrate washed with saturated NaHCO3 and water. The organic layer is dried (Na2 SO4) and evaporated in vacuo to give 21.2 g of the desired product. MS 379.1

Provenance & Evidence