Hydrochloric Acid → Tavaborole

Participants

Reaction Conditions

Reaction Steps

Dissolve 1-bromo-2-(1-ethoxy-ethoxymethyl)-4-fluoro-benzene(5.4 g, 19.5 mmol) in dry THF (100 mL) and cool to −78° C. under nitrogen. Add butyl lithium (2.5M in Hexanes, 10.2 mL, 25.4 mmol) dropwise at −78° C. Upon complete addition, stir the reaction at −78° C. for 10 minutes and then add trimethyl borate (4.4 mL, 39 mmol) and warm the reaction to room temperature. Pour the reaction into 1N HCl (100 mL) and stir for 1 hour. Extract the biphasic mixture with ether three times. Dry the combined organic layers with sodium sulfate, filter and concentrate in vacuo. Triturate the oily residue with cold hexanes to yield 2.1 g (70%) of the title compound as a white solid. 1H NMR (d6-DMSO) 9.18 (s, 1H), 7.70 (dd, J=8.2, 5.8 Hz, 1H), 7.20 (dd, J=9.5, 2.7 Hz, 1H), 7.11 (m, 1H), 4.92 (s, 1H).

Provenance & Evidence