Réaction #44599

Équation de réaction

cesium fluoride

dioxane

1-bromo-3,4,5-trifluorobenzene

trans-1-propen-1-ylboronic acid

→

title compound

Rendement 84.1%

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

Rendement 84.1%

Solvants

water

hexane

water

Conditions de réaction

Traitement

1. 1
   AutreThe resulting reaction solution
2. 2
   Températurecooled to room temperature
3. 3
   AutreThe precipitated insoluble matter was removed by filtration
4. 4
   Autrethe organic layer was separated
5. 5
   LavageThe obtained organic layer was washed with water
6. 6
   Autrethe insoluble matter was removed by filtration again
7. 7
   AutreThe organic layer was separated
8. 8
   LavageThe obtained organic layer was washed with water
9. 9
   Séchagewith saturated saline, dried over anhydrous magnesium sulfate
10. 10
    Concentrationconcentrated under reduced pressure
11. 11
    AutreThe residue was purified by silica gel column chromatography (eluting solvent: hexane)

Mode opératoire

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:

Source