반응 #7293

반응 방정식

1,4-dibromo-2,5-dimethoxybenzene

trimethylsilylacetylene

→

desired product

수율 73.8%

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

수율 73.8%

용매

diisopropylamine

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
   workup.DISSOLUTIONThe residue was dissolved in chloroform
6. 6
   세척resultant was washed with water several times
7. 7
   건조dried with anhydrous magnesium sulfate, which
8. 8
   여과was then filtered off
9. 9
   기타The solvent was removed
10. 10
    기타the residue was recrystallized from ethyl acetate/hexane mixture
11. 11
    기타to obtain pale yellow crystal, which
12. 12
    기타was sufficiently dried in a vacuum oven at 40° C.

실험 절차

100 g (0.338 mol) of 1,4-dibromo-2,5-dimethoxybenzene, 7.12 g (0.01 mol) of bistriphenylphospine palladium dichloride and 1.93 g (0.01 mol) of copper iodide were put into a 1 litter 3-neck round-bottom flask equipped with a stirrer, a thermometer and a reflux condenser under an argon atmosphere, and dissolved in 600 ml of diisopropylamine. 99 g (1 mol) of trimethylsilylacetylene was then slowly added dropwise at room temperature, and stirred at 80° C. for 12 hours. When the reaction was completed, the reaction mixture was cooled down to room temperature, generated salt was filtered off, and then the solvent was removed under a reduced pressure. The residue was dissolved in chloroform, and resultant was washed with water several times and then dried with anhydrous magnesium sulfate, which was then filtered off. The solvent was removed, and the residue was recrystallized from ethyl acetate/hexane mixture to obtain pale yellow crystal, which was sufficiently dried in a vacuum oven at 40° C. to give 82.5 g (yield: 73%) of the desired product, and its melting point was 164° C.–165° C.

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