反应详情

To triphenylphosphine dibromide (447.5 mg, 1.060 mmol), distilled dichloromethane (5 ml) was added under a nitrogen atmosphere and dissolved. Then a solution prepared by dissolving 1-bromo-4-(diallylethoxysilyl)benzene (11) (300 mg, 0.9637 mmol) into distilled dichloromethane (1.5 ml) was added and stirred at room temperature for 12 hours. After stirring, diethyl ether solution of 1M allylmagnesium bromide (1.156 ml, 1.156 mmol) was added dropwise and stirred at room temperature for 5 hours. The reacted mixture is cooled down to 0° C. and diluted with water to stop the reaction. 10% hydrochloric acid was added until salt was completely dissolved. The obtained organic layer was separated and the obtained water layer was extracted with dichloromethane. The collected organic layer was each washed with saturated sodium bicarbonate aqueous solution and saturated saline solution in this order, and dried over anhydrous magnesium sulfate and then filtered and concentrated under reduced pressure, obtaining a crude product. The crude product was passed through a silica gel short column (eluent: hexane/ethyl acetate=10/1), obtaining 1-bromo-4-(triallylsilyl)benzene (12) (yield: 256.4 mg, yield (%): 87%).

1. additionwas added under a nitrogen atmosphere
2. dissolutiondissolved
3. customThen a solution prepared
4. distillationinto distilled dichloromethane (1.5 ml)
5. additionwas added
6. stirringAfter stirring
7. stirringstirred at room temperature for 5 hours
8. temperatureThe reacted mixture is cooled down to 0° C.
9. customthe reaction
10. dissolutionwas completely dissolved
11. customThe obtained organic layer was separated
12. extractionthe obtained water layer was extracted with dichloromethane
13. washeach washed with saturated sodium bicarbonate aqueous solution and saturated saline solution in this order
14. dry with materialdried over anhydrous magnesium sulfate
15. filtrationfiltered
16. concentrationconcentrated under reduced pressure
17. customobtaining a crude product