Hydrochloric Acid → 4-fluoro-3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol

Participants

Reaction Steps

The crude 2-(3-fluoro-2-(2-(methoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was mixed with 25 ml of 6N HCl and the reaction mixture was stirred at rt overnight. The reaction was monitored by LC-MS. The reaction solution was extracted with EtOAc, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (5:1 to 2:1) to give 4-fluoro-3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (3.5 g, 52.5% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.17 (s, 1H), 7.30 (s, 1H), 7.08 (d, J=11.2 Hz, 1H), 2.34 (s, 3H), 1.49 (s, 6H) ppm.

Provenance & Evidence