反应详情

温度

85 °C

A 100-mL recovery flask containing 2-bromo-4-methoxypyridine (1.446 g, 7.69 mmol, purchased from Combi-Blocks, Inc.), 3-fluorophenylboronic acid (2.152 g, 15.38 mmol, purchased from Oakwood Products, Inc.), and 1,1′-bis(diphenylphosphino)ferrocene palladium(11)dichloride dichloromethane adduct (0.314 g, 0.385 mmol) was flushed with N2 and subsequently charged with dioxane (29 mL) and 1.9 M Na2CO3 in H2O (10 mL). The black-red mixture was stirred at 85° C. overnight. The next morning, after cooling to rt, the dark red mixture was diluted with H2O and extracted thrice with EtOAc. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to a black oil. Column chromatography (50 g Snap Ultra column, 10-100% EtOAc/hept) afforded 2-(3-fluorophenyl)-4-methoxypyridine (2.25 g, >99% yield) as a viscous yellow oil. m/z (ESI) 204.2 (M+H)+.

1. customwas flushed with N2
2. additionsubsequently charged with dioxane (29 mL) and 1.9 M Na2CO3 in H2O (10 mL)
3. temperatureThe next morning, after cooling to rt
4. additionthe dark red mixture was diluted with H2O
5. extractionextracted thrice with EtOAc
6. washwashed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo to a black oil