Sodium Carbonate → HCID 23220910, compound

Participants

Reaction Steps

In an 100 mL three-necked RB flask equipped with a magnetic bar, a condenser and a nitrogen gas inlet, 2-bromo-6-methoxynaphthalene (4.74 g, 20 mmol), 4-carboxybenzene boronic acid (3.50 g, 20 mmol) and 1-propanol (40 mL) were mixed and stirred at room temperature for approximately 30 min. Palladium acetate (0.014 g, 0.003 equiv., 0.06 mmol), triphenylphosphine (0.047 g, 0.009 equiv., 0.18 mmol), Na2CO3 solution (2M, 12 mL, 1.20 equiv., 24 mmol) and water (8 mL) were added and the mixture was refluxed for 1.5 h. When the mixture was still hot, 25 mL of water was added and the mixture was stirred and cooled to room temperature. The resultant crystals were filtered, washed with water and refluxed with 50 mL of acetic acid for 3-4 h. A white solid was obtained (5.08 g) and recrystallization from acetone showed the title compound as white crystals (4.63 g, 83%). mp 288-289° C. 1H NMR (500 MHz, DMSO) δ 3.90 (s, 3H), 7.2-8.3 (m, 10H), 12.99 (s, 1H). IR (KBr) ν (cm−1): 2500-3000 (COO—H, very broad, m), 1030 (OCH3, s), 1678 (C═O, s). Anal. Calcd for C18H14O3: C, 77.68; H, 5.07. Found: C, 77.56; H, 5.08.

Provenance & Evidence