Potassium Carbonate → HCID 71245628, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-hydroxy-acetophenone (0.3 g, 2.2 mmol), 4-bromomethylphenylboronic acid pinacol ester (0.8 g, 2.7 mmol) and potassium carbonate (0.3 g, 2.2 mmol) in DMF (5 ml) was heated up to 110° C. for 24 h. The reaction mixture composition was determined by TLC and 4-bromomethylphenylboronic acid pinacol ester (0.3 g, 1.0 mmol) was added. The reaction mixture was heated to 110° C. for additional 24 h. The solvent was removed in vacuo. The crude product was purified by column chromatography on silica (CH2Cl2 to 4% MeOH) to give the desired product as an oil (0.51 g, 1.4 mmol, 64%). δH (CDCl3, 400 MHz): 1.24 (12H, s, CH3), 2.59 (3H, s, COCH3), 6.98 (1H, dd, 3J=9.2, 4J=1.6), 7.00 (1H, dd, 3J=8.4, 4J=0.8), 7.41 (1H, dd, 4J=4), 7.43 (2H, d, 3J=8.4), 7.74 (1H, dd, 3J=7.6, 4J=1.6), 7.83 (2H, d). δC (CDCl3, 125 MHz): 24.91 (CH3), 32.15 (COCH3), 70.62 (Cqart), 83.95 (CH2), 112.80 (CAr), 120.93 (CAr), 126.78 (CAr), 128.72 (CAr), 130.52 (CAr), 133.62 (CAr), 135.16 (CAr), 139.23 (CAr), 158.00 (CAr), 199.93 (CO). m/z (ES+) 391.1 [M+K]+ calc for C21H25BKO4391.2.

Provenance & Evidence