反应详情

温度

130 °C

To a microwave reaction vessel was added a mixture of 1-bromo-2,5-dimethyl-4-nitrobenzene (1.15 g, 5.0 mmol), dibutyl vinylboronate (1.16 g, 6.3 mmol), Pd(PPh3)4(289 mg, 0.25 mmol), CsF (2.28 g, 15 mmol) and a mixed solvent (1,2-dimethoxyethane/MeOH=2:1, 15 mL). The mixture was degassed and sealed with N2. The reaction vessel was then heated to 130° C. in a microwave reactor for 15 min. After opening the reaction vessel, the mixture was poured into saturated NH4Cl aqueous solution (30 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine and dried (MgSO4). After removing the drying agent by filtration, the filtrate was concentrated and purified by flash column chromatography (silica gel, 0-30% EtOAc in hexanes gradient) to provide 1,4-dimethyl-2-nitro-5-vinylbenzene as needlelike crystals; ESMS m/z 178.1 (M+H+).

1. customTo a microwave reaction vessel
2. additionwas added
3. customThe mixture was degassed
4. customsealed with N2
5. additionthe mixture was poured into saturated NH4Cl aqueous solution (30 mL)
6. extractionextracted with EtOAc (3×50 mL)
7. washThe combined organic layers were washed with brine
8. dry with materialdried (MgSO4)
9. customAfter removing the drying agent
10. filtrationby filtration
11. concentrationthe filtrate was concentrated
12. custompurified by flash column chromatography (silica gel, 0-30% EtOAc in hexanes gradient)