反应详情

温度

90 °C

To a solution of 5-bromo-6-chloro-nicotinic acid methyl ester (10 g, 40 mmol) in toluene (200 mL) was added 4-chlorophenyl-boronic acid (6.4 g, 40 mmol), [1,1′-bis(diphenylphosphino)ferrrocene]dichlorpalladium(II) dichloromethane complex (1.6 g, 2 mmol) and 2 M sodiumcarbonate solution (60 mL). The reaction mixture was stirred for 2 h at 90° C. After cooling, the phases were separated; the aqueous phase was extracted once with ethyl acetate (200 mL), organic phases were washed once with water and brine (150 mL each), combined and dried over MgSO4. After evaporation of the solvent the crude product was purified by flash column chromatography (dichloromethane/heptane 2:1 to 9:1) to give 6-chloro-5-(4-chloro-phenyl)-nicotinic acid methyl ester as a colorless solid, 8.12 g (72% yield). m/z (ES+): 281.1, 283.1 (M+H).

1. temperatureAfter cooling
2. customthe phases were separated
3. extractionthe aqueous phase was extracted once with ethyl acetate (200 mL), organic phases
4. washwere washed once with water and brine (150 mL each)
5. dry with materialdried over MgSO4
6. customAfter evaporation of the solvent the crude product
7. customwas purified by flash column chromatography (dichloromethane/heptane 2:1 to 9:1)