반응 #7292

반응 방정식

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

phenylacetylene

→

desired product

수율 75.7%

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

수율 75.7%

용매

piperidine

반응 조건

후처리

1. 1
   기타equipped with a stirrer
2. 2
   온도the reaction mixture was cooled down to room temperature
3. 3
   여과was filtered off
4. 4
   기타The solvent was removed under a reduced pressure
5. 5
   추출the residue was extracted with methylene chloride
6. 6
   세척Organic layer was washed with water several times
7. 7
   건조dried with anhydrous magnesium sulfate
8. 8
   기타the solvent was removed
9. 9
   기타to obtain yellow solid
10. 10
    기타This solid was recrystallized from ethyl acetate
11. 11
    기타to obtain yellow crystal, which
12. 12
    기타was sufficiently dried in a vacuum oven at 40° C.

실험 절차

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.

출처