Реакция #44599

Уравнение реакции

cesium fluoride

dioxane

1-bromo-3,4,5-trifluorobenzene

trans-1-propen-1-ylboronic acid

→

title compound

Выход 84.1%

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

Выход 84.1%

Растворители

water

hexane

water

Условия реакции

Обработка

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

Методика

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:

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