Hydrochloric Acid → 6-fluoro-3,3,5-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol

Participants

Reaction Steps

To a solution of 2-(2-(2-(ethoxymethoxy)propan-2-yl)-5-fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.35 g, 6.68 mmol) in THF (67 mL) was added 6 N HCl (67 mL). The reaction mixture was stirred at room temperature overnight, and extracted with DCM (200 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with PE-EA (from 10:1 to 3:1) to give 6-fluoro-3,3,5-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (835 mg, 64%) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.189 (d, J=8.0 Hz, 1H), 6.995 (d, J=6.5 Hz, 1H), 5.950 (s, 1H), 2.266 (s, 3H), 1.472 (s, 6H) ppm.

Provenance & Evidence