Реакция #44631

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 insoluble matter was removed by filtration
4. 4
   ДругоеThe organic layer of the filtrate was separated
5. 5
   Промывкаwashed with water
6. 6
   ДругоеThe insoluble matter was removed by filtration again
7. 7
   ПромывкаThe filtrate was washed with water
8. 8
   Сушкаwith saturated saline, dried over anhydrous magnesium sulfate
9. 9
   Концентрированиеconcentrated under reduced pressure
10. 10
    ДругоеThe residue was purified by silica gel column chromatography (hexane)

Методика

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:

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