Trimethyl borate → (3-hydroxyphenyl)boronic Acid

Participants

Reaction Steps

3-Bromophenol (8.65 g, 50 mmol) in dry THF (150 mL) was treated with sodium hydride (60%, 2.4 g, 60 mmol) at r.t. After 1 h, sec-butyllithium (1.3 M, 50 mL, 65 mmoL) was added dropwise to the reaction solution at −78° C. The reaction mixture was then allowed to stir at the same temperature for 30 min prior to addition of trimethyl borate (15 mL). After warming up to r.t. for 2 hrs, the reaction mixture was quenched with water (50 mL), and extracted with dichloromethane (2×100 mL). The combined organic phases were dried over MgSO4 and evaporated to give the title compound as a white solid (4.0 g, 58%), which was used in the Suzuki coupling reactions without further purification.

Provenance & Evidence