2,5-Dibromopyridine → HCID 71003252, compound

Participants

Reaction Conditions

Reaction Steps

n-BuLi was added dropwise to a solution of 2,5-dibromopyridine in toluene (30 mL) at −78° C. The reaction mixture was stirred for 1 hour at −78° C., then a solution of methyl 2,2-dimethyl-4-oxocyclohexanecarboxylate in toluene (5 mL) was added. The reaction mixture was warm to room temperature, quenched with saturated aqueous ammonium chloride, extracted with CH2C12 (3×), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to afford methyl 4-(5-bromopyridin-2-yl)-4-hydroxy-2,2-dimethylcyclohexanecarboxylate as a colorless oil. MS ESI calc'd for C15H21BrNO3 [M+H]+ 342 and 344. found 342 and 344.

Provenance & Evidence