반응 #44631

반응 방정식

cesium fluoride

dioxane

1-bromo-3,4,5-trifluorobenzene

trans-1-propen-1-ylboronic acid

→

title compound

수율 84.1%

1,2,3-trifluoro-5-((E)-propenyl)benzene

수율 84.1%

용매

water

hexane

water

반응 조건

후처리

1. 1
   기타The resulting reaction solution
2. 2
   온도cooled to room temperature
3. 3
   기타The insoluble matter was removed by filtration
4. 4
   기타The organic layer of the filtrate was separated
5. 5
   세척washed with water
6. 6
   기타The insoluble matter was removed by filtration again
7. 7
   세척The filtrate was washed with water
8. 8
   건조with saturated saline, dried over anhydrous magnesium sulfate
9. 9
   농축concentrated under reduced pressure
10. 10
    기타The residue was purified by silica gel column chromatography (hexane)

실험 절차

In nitrogen atmosphere, tetrakistriphenylphosphine palladium(0) (4.66 g) and cesium fluoride (21.4 g) were added to a solution mixture of dioxane (95 mL) and water (5 mL) of 1-bromo-3,4,5-trifluorobenzene (8.5 g) and trans-1-propen-1-ylboronic acid (4.1 g). The resulting reaction solution was stirred at 80° C. for 5 hr and then cooled to room temperature, and hexane and water were added thereto. The insoluble matter was removed by filtration. The organic layer of the filtrate was separated and washed with water. The insoluble matter was removed by filtration again. The filtrate was washed with water and then with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane) to give 5.83 g of the title compound. The physical property values of this compound were as follows:

출처