2,6-Dibromopyridine → 1-(6-Bromopyridin-2-yl)cyclobutanol

Participants

Reaction Steps

n-Butyllithium (6.85 mL, 11.0 mmol) was added to a suspension of 2,6-dibromopyridine (2.36 g, 9.96 mmol) in dichloromethane (60 mL) at −78° C. The reaction mixture was stirred for 15 minutes and cyclobutanone (0.838 g, 12.0 mmol) was added in one portion at −78° C. The reaction was stirred for an additional 30 minutes before pouring the reaction into a mixture of saturated aqueous NH4Cl and dichloromethane. The organic layer was concentrated to dryness and was purified by flash chromatography to yield 1-(6-bromopyridin-2-yl)cyclobutanol as a light yellow oil. MS ESI calc'd. for C9H11BrNO [M+H]+ 228 and 230. found 228 and 230.

Provenance & Evidence