Reaction #44631

Reaction equation

cesium fluoride

dioxane

1-bromo-3,4,5-trifluorobenzene

trans-1-propen-1-ylboronic acid

→

title compound

Yield 84.1%

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

Yield 84.1%

Solvents

water

hexane

water

Conditions

Workup

1. 1
   OtherThe resulting reaction solution
2. 2
   Temperaturecooled to room temperature
3. 3
   OtherThe insoluble matter was removed by filtration
4. 4
   OtherThe organic layer of the filtrate was separated
5. 5
   Washwashed with water
6. 6
   OtherThe insoluble matter was removed by filtration again
7. 7
   WashThe filtrate was washed with water
8. 8
   Dryingwith saturated saline, dried over anhydrous magnesium sulfate
9. 9
   Concentrationconcentrated under reduced pressure
10. 10
    OtherThe residue was purified by silica gel column chromatography (hexane)

Procedure

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:

Source