反应详情

温度

80 °C

Under an argon atmosphere, 40 g (0.155 mol) of 9-bromoanthracene, 3.3 g (4.6 mmol) of bis(triphenylphosphine)palladium(II) dichloride and 0.87 g (3 mmol) of copper Iodide were dissolved in 500 ml of diisopropylamine in a 1 L 3-necked flask equipped with a stirrer, thermometer and reflux condenser. 23 g (0.233 mol) of trimethylsilyl acetylene was then slowly dropped into the resulting mixture at room temperature. The reaction mixture was slowly heated to 80° C. and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled down to room temperature, and then the precipitated salt was filtered off. The solvent was removed under a reduced pressure, and then the residue was dissolved in methylene chloride. The organic layer was washed with water several times and then dried with anhydrous magnesium sulfate. The solvent was removed to obtain orange-colored liquid, which was purified by silica gel column chromatography using hexane as an eluent, and then recrystallized from ethanol to give yellow crystal. The yellow crystal was recovered and sufficiently dried in a vacuum oven at 40° C., to give 32 g (83.3% yield) of the desired product having a melting point of 66-68° C.

1. customequipped with a stirrer
2. temperaturethermometer and reflux condenser
3. temperaturerefluxed for 12 hours
4. temperaturethe reaction mixture was cooled down to room temperature
5. filtrationthe precipitated salt was filtered off
6. customThe solvent was removed under a reduced pressure
7. dissolutionthe residue was dissolved in methylene chloride
8. washThe organic layer was washed with water several times
9. dry with materialdried with anhydrous magnesium sulfate
10. customThe solvent was removed
11. customto obtain orange-colored liquid, which
12. customwas purified by silica gel column chromatography
13. customrecrystallized from ethanol
14. customto give yellow crystal
15. customThe yellow crystal was recovered
16. customsufficiently dried in a vacuum oven at 40° C.