Triisopropyl borate → (5-Bromo-2-(diisopropylcarbamoyl)phenyl)boronic acid

Participants

Reaction Steps

To a solution of 4-bromo-N,N-diisopropylbenzamide (1.0 g, 35 mmol) and triisopropyl borate (0.79 g, 4.2 mmol) in THF (20 mL) was added a freshly prepared solution of LDA in THF (4.6 mL, 4.6 mmol) dropwise at 20° C. over a 1 hour period under nitrogen. The reaction mixture was stirred overnight, quenched with saturated aqueous NH4Cl solution (20 mL), and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (20 mL), dried over magnesium sulfate, filtered and concentrated to afford {5-bromo-2-[(diisopropylamino)carbonyl]phenyl}boronic acid that was used without further purification.

Provenance & Evidence