2,5-Dibromopyridine → HCID 86638499, compound

Participants

Reaction Steps

To the solution of 2,5-dibromopyridine (16 g, 67 mmol) in toluene (150 mL) was added 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). The mixture was stirred at ambient temperature for 16 hours, then diluted with saturated aqueous NH4Cl (80 mL) at 0° C., and extracted with EtOAc (2×100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel (eluting with 5-10% EtOAc/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