Pinacol → Phenylboronic acid pinacol ester

Participants

Reaction Conditions

Reaction Steps

Phenyl boronic acid (100 g, 0.82 mol, 1 equiv.) and pinacol (96.92 g, 0.82 mol, 1 equiv.) were dissolved in toluene (500 mL) at room temperature. The cloudy solution was then placed on to a rotary evaporator and stirred for 2 hours at 60° C. After this period the solid had dissolved, concurrent with the formation of water (ca. 29.5 mL) as a second layer. The water was then removed in a separating funnel and the crude reaction filtered through Celite. Evaporation of the solvent yielded a clear pale yellow oil which solidified on cooling in a refrigerator to give the title compound in a near-quantitative yield as a white solid (ca. 167 g).

Provenance & Evidence