3-(N,N-Dimethylaminocarbonyl)phenylboronic acid, pinacol ester

Synthesis

18469-37-9

73183-34-3

400727-57-3

GENERAL STEPS: A mixture of bis(pinacolato)diboron (610 mg, 2.4 mmol), 4-bromo-N,N-dimethylbenzamide (2,500 mg, 2.19 mmol), Pd(dppf)Cl2 (18 mg, 0.02 mmol) and KOAc (320 mg, 3.3 mmol) was dissolved in 1,4-dioxane (18 mL) in. The reaction mixture was heated and stirred at 100 °C for 16 h under nitrogen protection. Upon completion of the reaction, the reaction mixture was filtered and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using CH2Cl2 solution with 0-5% MeOH as eluent to afford the target product 4-(dimethylcarbamoyl)phenylboronic acid pinacol ester (540 mg, 90% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.86-7.78 (m, 2H), 7.43-7.36 (m, 2H), 3.11 (s, 3H), 2.97 (s, 3H), 1.35 (s, 12H).

References