反応 #44599

反応方程式

cesium fluoride

dioxane

1-bromo-3,4,5-trifluorobenzene

trans-1-propen-1-ylboronic acid

→

title compound

収率 84.1%

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

収率 84.1%

溶媒

water

hexane

water

反応条件

後処理

1. 1
   その他The resulting reaction solution
2. 2
   温度cooled to room temperature
3. 3
   その他The precipitated insoluble matter was removed by filtration
4. 4
   その他the organic layer was separated
5. 5
   洗浄The obtained organic layer was washed with water
6. 6
   その他the insoluble matter was removed by filtration again
7. 7
   その他The organic layer was separated
8. 8
   洗浄The obtained organic layer was washed with water
9. 9
   乾燥with saturated saline, dried over anhydrous magnesium sulfate
10. 10
    濃縮concentrated under reduced pressure
11. 11
    その他The residue was purified by silica gel column chromatography (eluting solvent: hexane)

実験手順

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:

出典