反応 #44631

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 insoluble matter was removed by filtration
4. 4
   その他The organic layer of the filtrate was separated
5. 5
   洗浄washed with water
6. 6
   その他The insoluble matter was removed by filtration again
7. 7
   洗浄The filtrate was washed with water
8. 8
   乾燥with saturated saline, dried over anhydrous magnesium sulfate
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他The residue was purified by silica gel column chromatography (hexane)

実験手順

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:

出典