2,5-Dibromopyridine → HCID 86638499, compound

Participants

Reaction Steps

To a solution of 2,5-dibromopyridine (16 g, 67 mmol) in toluene (150 mL) was added 2.5 N solution of n-BuLi (27 mL, 67 mmol) dropwise at −78° C. The resulting solution was stirred at −78° C. for 1 hour before the addition of 2,2-difluoroacetate (10 g, 80 mmol). After stirred at ambient temperature overnight, the reaction solution was diluted with saturated aqueous NH4Cl solution (80 mL) at 0° C., and then extracted with ethyl acetate (2×100 mL). All the organic solution was dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography with 5-10% ethyl acetate in hexane to afford the title compound as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.82 (s, 1H), 8.08 (d, J=6.0 Hz, 1H), 8.03 (d, J=6.0 Hz, 1H), 7.05 (t, J=54.4 Hz, 1H).

Provenance & Evidence