89291-23-6

121-43-7

698-00-0

89291-23-6

The general procedure for the synthesis of 2-(dimethylamino)benzeneboronic acid from trimethyl borate and 2-bromo-N,N-dimethylaniline is as follows: dissolve N,N-dimethyl-o-bromoaniline (4 g, 20 mmol) in anhydrous tetrahydrofuran (100 mL) at -78 °C, slowly add 2.5 M n-butyllithium solution (10 mL, 25 mmol) dropwise, and leave it at that temperature with continuous stirring for 2 hours. Subsequently, trimethyl borate (2.6 g, 25 mmol) was added to the reaction mixture and stirring was continued for 2 hours. Upon completion of the reaction, the mixture was slowly warmed to room temperature and the reaction was terminated by the addition of 0.1 N hydrochloric acid solution (200 mL). The reaction mixture was extracted with dichloromethane (150 mL x 3) and the organic phases were combined and washed with water (150 mL x 3). Finally, the organic phase was concentrated under reduced pressure to afford the target product 2-(dimethylamino)phenylboronic acid (3.0 g, 91% yield). The product was analyzed by LC-MS (ESI) and showed m/z = 166 [M + H]+.