Cyclobutanone → 1-(5-Bromopyridin-2-yl)cyclobutan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,5-dibromopyridine (4.74 g, 20.0 mmol) in toluene (200 mL) was added n-BuLi (1.2 eq) dropwise at −50° C. The mixture was stirred at that temperature for 40 min, then cooled to −78° C. before cyclobutanone (1.82 g, 26.0 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h, then warmed to 0° C. and quenched with 40 mL of NH4Cl (sat.). The organic layer was separated and concentrated. The crude product was purified by a SiO2 column (0-40% EtOAc/Hexanes, Rf=0.7 in 50% EtOAc) to afford the titled compound as a red oil (3.11 g).

Provenance & Evidence