(3-acrylamidophenyl)boronic acid

30418-59-8

814-68-6

99349-68-5

General procedure for the synthesis of 3-acrylamidophenylboronic acid from 3-aminophenylboronic acid and acryloyl chloride: 3-aminophenylboronic acid (0.566 g, 3.65 mmol) and Na2CO3 (0.67 g, 80.3 mmol) were added to 20 mL of a 1:1 (v/v) solvent mixture of tetrahydrofuran and water and the mixture was cooled to 0 °C. Acryloyl chloride (960 mg, 8.06 mmol) was slowly added dropwise under stirring conditions. After the dropwise addition, the mixture was allowed to warm up naturally to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, 10 mL of water was added to terminate the reaction, followed by extraction of the reaction mixture with ethyl acetate (20 mL x 3). The organic phases were combined, washed with saturated NaCl solution (10 mL) and finally the organic layer was dried with anhydrous Na2SO4. After concentrating the organic layer, it was purified by column chromatography to give the light yellow solid product 3-acrylamidophenylboronic acid (0.32 g, 40.1% yield).