Boric acid (H3BO3), tripropyl ester → 3-Benzyloxy-phenylboronic acid

Participants

Reaction Conditions

Reaction Steps

20 g (76 mmol) of 3-Benzyloxybromobenzene was dissolved in 200 mL of anhydrous THF and cooled to -78° C. under a nitrogen atmosphere. To the stirring solution, 90 mL of 1.6 M n-BuLi (83.6 mmol) was slowly added. After several minutes, 33.6 mL (83.6 mmol) tripropylborate was added and the reaction was allowed to slowly warm to ambient temperature over the next four hours. The reaction was quenched with the addition of 400 mL of 1N HCl. The reaction mixture was extracted three times with EtOAc. The EtOAc solution was washed twice with brine, dried with Na2SO4, and evaporated to dryness. The final product was crystallized from EtOAc-hexane. This yielded 10 g of the title compound as a white solid.

Provenance & Evidence