反应 #7292

反应方程式

1,4-dibromo-2,5-dimethoxy benzene

phenylacetylene

→

desired product

收率 75.7%

1,4-bis(phenylethynyl)-2,5-dimethoxybenzene

收率 75.7%

溶剂

piperidine

反应条件

后处理

1. 1
   其他equipped with a stirrer
2. 2
   温度the reaction mixture was cooled down to room temperature
3. 3
   过滤was filtered off
4. 4
   其他The solvent was removed under a reduced pressure
5. 5
   萃取the residue was extracted with methylene chloride
6. 6
   洗涤Organic layer was washed with water several times
7. 7
   干燥dried with anhydrous magnesium sulfate
8. 8
   其他the solvent was removed
9. 9
   其他to obtain yellow solid
10. 10
    其他This solid was recrystallized from ethyl acetate
11. 11
    其他to obtain yellow crystal, which
12. 12
    其他was sufficiently dried in a vacuum oven at 40° C.

实验过程

50 g (160 mmol) of 1,4-dibromo-2,5-dimethoxy benzene, 3.6 g (0.005 mol) of bistriphenylphosphine palladium dichloride and 0.97 g (0.005 mol) of copper iodide were put into a 1 litter 3-neck flask equipped with a stirrer, a thermometer and a reflux condenser under an argon atmosphere, and dissolved in 500 ml of piperidine. 43 g (0.422 mol) of phenylacetylene was then slowly added dropwise at room temperature. The reaction temperature was slowly raised to 80° C. and then the reaction mixture was stirred at the same temperature for 12 hours. When the reaction was completed, the reaction mixture was cooled down to room temperature, and then generated salt was filtered off. The solvent was removed under a reduced pressure, and then the residue was extracted with methylene chloride. Organic layer was washed with water several times and dried with anhydrous magnesium sulfate, and then the solvent was removed to obtain yellow solid. This solid was recrystallized from ethyl acetate to obtain yellow crystal, which was sufficiently dried in a vacuum oven at 40° C. to give 41 g (yield: 72%) of the desired product, and its melting point was 172° C.–174° C.

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