반응 #44599

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 precipitated insoluble matter was removed by filtration
4. 4
   기타the organic layer was separated
5. 5
   세척The obtained organic layer was washed with water
6. 6
   기타the insoluble matter was removed by filtration again
7. 7
   기타The organic layer was separated
8. 8
   세척The obtained organic layer was washed with water
9. 9
   건조with saturated saline, dried over anhydrous magnesium sulfate
10. 10
    농축concentrated under reduced pressure
11. 11
    기타The residue was purified by silica gel column chromatography (eluting solvent: hexane)

실험 절차

In nitrogen atmosphere, tetrakistriphenyl-phosphine 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), trans-1-propen-1-ylboronic acid (4.1 g). The resulting reaction solution was stirred at 80° C. for 5 hr and cooled to room temperature. To the reaction solution, hexane and water were added. The precipitated insoluble matter was removed by filtration, and the organic layer was separated. The obtained organic layer was washed with water, and the insoluble matter was removed by filtration again. The organic layer was separated. The obtained organic layer 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 (eluting solvent: hexane) to give 5.83 g of the title compound. The physical property values of this compound were as follows:

출처