Sodium Hydroxide → 2-Methoxy-7-(4-methoxyphenyl)naphthalene

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Reaction Steps

A mixture of 7-methoxy-2-naphthyl trifluoromethanesulfonate (3.15 g, 10.3 mmol), 4-methoxy-phenylboronic acid (2.2 g, 14 mmol) sodium carbonate (10 mL of 2N aqueous solution), tetrakis(triphenylphosphine)palladium (0.59 g, 0.05 mmol), and 100 mL ethylene glycol dimethyl ether were heated to reflux for 8 hr. The mixture was cooled to room temperature and poured into 100 mL of 1N NaOH, The mixture was extracted with ethyl acetate (3×250 mL), washed with brine (2×100 mL), dried over magnesium sulfate, filtered, evaporation of the solvent and purification by silica chromatography (5%–10% ethyl adetate-hexanes) yielded 2.17 g (79%) of the title compound as a white solid: mp 154° C.; 1H NMR (CDCl3): δ 3.87 (3H, s), 3.94 (3H, s), 7.02 (2H, d, J=8.72 Hz), 7.13 (1H, dd, J=2.54 Hz, J=9.09 Hz), 7.18 (1H, J=2.55 Hz), 7.56 (1H, dd, J=1.82 Hz, J=8.36 Hz), 7.65 (2H, d, J=8.72 Hz), 7.74 (1H, d, J=9.09 Hz), 7.81 (1H, d, J=8.36 Hz), 7.89 (1H, d, J=1.09 Hz); MS (EI) m/z 264 (M).

Provenance & Evidence