反应详情

To a mixture of 2-bromo-6-methoxynaphthalene (23.79 g, 100.3 mmol) and tetrakis(triphenylphosphine)palladium (5.8 g, 5 mmol) was added a solution of 4-methoxyphenylmagnesium bromide in THF (400 mL of 0.5 N solution, 200 mmol). The stirred solution was heated to reflux for 3 hr, cooled to RT, and stirred into 200 mL of 1 N HCl. The mixture was extracted with dichloromethane and filtered through a short silica plug with dichloromethane. The solvent was removed to yield a crude yellow solid which was further purified by silica chromatography (20-50% ethyl acetate-hexanes) to yield 25.68 g (97%) of the title compound as a white solid: mp 190° C.; 1H NMR (CDCl3): δ 3.86 (3H, s), 3.93 (3H, s), 7.01 (2H, d, J=8.57 Hz), 7.14-7.18 (2H, m), 7.63 (2H, d, J=8.50 Hz), 7.67 (1H, dd, J=1.68 Hz, J=8.73 Hz), 7.76-7.80 (2H, m), 7.91 (1H, d, J=0.94 Hz); MS (ESI) m/z265 (M+H)+.

1. temperatureThe stirred solution was heated
2. temperatureto reflux for 3 hr
3. extractionThe mixture was extracted with dichloromethane
4. filtrationfiltered through a short silica plug with dichloromethane
5. customThe solvent was removed
6. customto yield a crude yellow solid which
7. customwas further purified by silica chromatography (20-50% ethyl acetate-hexanes)