Potassium Carbonate → HCID 11324480, compound

Participants

Reaction Steps

2,4-Dimethoxyphenylboronic acid (24 g, 134 mmol) was dissolved in ethanol (250 mL). The compound from Step A (21 g, 67 mmol) was dissolved in 1,2-dimethoxyethane (375 mL). The two solutions were mixed with tetrakis(triphenylphosphine)palladium (1 g, 0.9 mmol) and K2CO3 (8.9 g, 64 mmol). The resulting suspension was refluxed for 2 h and then poured into saturated NaHCO3 (1 L). The reaction mixture was extracted three times with CH2Cl2 (400 mL) and dried over Na2SO4. The solvent was removed to yield 35.6 g of crude product which was chromatographed on silica gel with hexane/ethyl acetate (2:1) followed by hexane/ethyl acetate (1:1) to yield 18.3 g (87%) of the title compound. 1H-NMR (400 MHz, CDCl3) δH 2.68 (3H, s, COCH3), 3.73 (3H, s, OCH3), 3.76 (3H, s, OCH3), 3.88 (3H, s, CO2CH3), 6.52 (1H, s ArH), 6.62 (1H, d, ArH), 7.23 (1H, d, ArH), 7.45 (1H, d, ArH), 8.13 (1H, d, ArH), 8.42 (1H, s, ArH).

Provenance & Evidence