反应详情

8-Bromo-6-isopropylquinoline (1.15 g) was dissolved in 46 mL of ethanol/benzene (1:1). 3-Nitrobenzene boronic acid (1.4 g), Na2CO3 (2M, 9.2 mL) and tetrakistriphenylphosphine palladium (0.23 g) were added successively. The reaction mixture was refluxed for 6 hours and then cooled and concentrated. The resulting residue was partitioned between 75 mL H2O and 100 mL of ethyl acetate, and extracted with ethyl acetate (2×100 mL). The extracts were then dried over MgSO4, filtered, concentrated and chromatographed on silica gel (20:80 ethyl acetate:hexane) yielding 1.2 g of 6-isopropyl-8-(3-nitrophenyl)quinoline as a slightly impure yellow oil.

1. temperatureThe reaction mixture was refluxed for 6 hours
2. temperaturecooled
3. concentrationconcentrated
4. customThe resulting residue was partitioned between 75 mL H2O and 100 mL of ethyl acetate
5. extractionextracted with ethyl acetate (2×100 mL)
6. dry with materialThe extracts were then dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customchromatographed on silica gel (20:80 ethyl acetate:hexane)