反应详情

A 100-mL, round-bottomed flask, fitted with a reflux condenser was charged with 2,5-dichloropyridine (1.00 g, 6.76 mmol), phenylboronic acid (1.07 g, 8.78 mmol), [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.204 g, 0.338 mmol), argon-degassed toluene/ethanol (4:1, 17 mL) and argon-degassed aqueous 1 N sodium carbonate (6.6 mL). The mixture was heated to reflux for 3 h, cooled to room temperature and diluted with water (15 mL) and EtOAc (100 mL). The layers separated and the aqueous phase was extracted with EtOAc (100 mL). The combine organic extracts were dried over Na2SO4, filtered and concentrated. Purification by flash column chromatography (silica gel, 50:50 hexanes/CH2Cl2) provided 5-chloro-2-phenylpyridine (0.959 g, 75%) as a white solid.

1. customA 100-mL, round-bottomed flask, fitted with a reflux condenser
2. customdegassed toluene/ethanol (4:1, 17 mL) and argon-
3. customdegassed aqueous 1 N sodium carbonate (6.6 mL)
4. temperatureThe mixture was heated
5. temperatureto reflux for 3 h
6. additiondiluted with water (15 mL) and EtOAc (100 mL)
7. customThe layers separated
8. extractionthe aqueous phase was extracted with EtOAc (100 mL)
9. dry with materialThe combine organic extracts were dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customPurification by flash column chromatography (silica gel, 50:50 hexanes/CH2Cl2)