反应详情

To a flask containing a bi-phasic mixture of 2-bromo-4-nitroanisole (15.0 g, 64.6 mmol) and 3-chlorophenylboronic acid (12.1 g, 77.6 mmol) in ethylene glycol dimethyl ether (187.5 mL) and 2.0 N aqueous cesium carbonate (97 mL) was added 1-1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II), complex with dichloromethane (1:1) (1.5 g). The mixture was heated at reflux for 4 hours under a nitrogen atmosphere. The crude reaction mixture was partitioned between ethyl acetate (350 mL) and brine (250 mL) and then filtered through a Buchner funnel. Layers were separated and the organic layer was washed with brine (250 mL). The organic phase was dried over Na2SO4, filtered, and concentrated to a dark oil. The crude residue was purified by flash chromatography on silica gel using dichloromethane as the eluent to afford 2-(3-chlorophenyl)-4-nitroanisole as a yellow solid (13.9 g, 59.4 mmol).

1. additionTo a flask containing
2. temperatureThe mixture was heated
3. temperatureat reflux for 4 hours under a nitrogen atmosphere
4. customThe crude reaction mixture
5. customwas partitioned between ethyl acetate (350 mL) and brine (250 mL)
6. filtrationfiltered through a Buchner funnel
7. customLayers were separated
8. washthe organic layer was washed with brine (250 mL)
9. dry with materialThe organic phase was dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated to a dark oil
12. customThe crude residue was purified by flash chromatography on silica gel