Ammonium Chloride → HCID 86730297, compound

Participants

Reaction Steps

To a solution of 1-(5-bromopyridin-2-yl)-2,2-difluoroethanone (1.5 g, 6.4 mmol) in THF (15 mL) under nitrogen was added MeMgBr (3.2 mL, 9.6 mmol, 3.0 M in THF) dropwise at −15° C. The resulting solution was stirred at ambient temperature for 2 hours before the addition of saturated aqueous NH4Cl (10 mL) at 0° C. The resulting mixture was vigorously stirred for 10 minutes, and then extracted with EtOAc (3×20 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 1-3% EtOAc/hexane) to afford the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.83 (d, J=2.0 Hz, 1H), 7.92 (dd, J=8.4, 2.0 Hz, 1H), 7.43 (d, J=8.4 Hz, 1H), 5.76 (t, J=56.4 Hz, 1H), 5.22 (br, 1H), 1.60 (s, 3H).

Provenance & Evidence