2-Bromopyridine → 2-(Tributylstannyl)pyridine

Participants

Reaction Conditions

Reaction Steps

2-bromopyridine (3.3 g, 21.0 mmol) was placed in a reaction flask. To ensure a nitrogen atmosphere in the reaction flask, the gas in the reaction flask was drawn out and the reaction flask was refilled with nitrogen gas in a rapid manner three times. To the reaction flask, 30 ml of anhydrous tetrahydrofuran was added, and then 9 ml of an n-butyllithium solution (23.0 mmol, 2.5 M in n-hexane) was slowly added at −78° C. to obtain a mixture. The mixture was kept at −78° C. and stirred for 60 minutes. At this moment, the color of the mixture changed from clear dark brown to cloudy yellowish green. Next, tributyltin chloride (6.3 ml, 23.0 mmol) was slowly added to the mixture at −78° C. for reaction for 3 hours. Thereafter, the temperature of the mixture was raised to 20° C., and the mixture was continuously stirred for 30 minutes to allow the color of the mixture to change to clear yellow. Then, a saturated ammonium chloride (NH4Cl) aqueous solution was slowly added to the mixture to terminate the reaction. The solvents in the mixture were drawn out of the reaction flask, and the residue in the reaction flask was washed several times with ethyl acetate and with a saturated sodium chloride aqueous solution to collect an organic layer. The organic layer was dehydrated using sodium sulfate (Na2SO4) to obtain a dark brown liquid (7.53 g, 98% yield).

Provenance & Evidence