تفاعل #44599

معادلة التفاعل

cesium fluoride

dioxane

1-bromo-3,4,5-trifluorobenzene

trans-1-propen-1-ylboronic acid

→

title compound

المردود 84.1%

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

المردود 84.1%

المذيبات

water

hexane

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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:

المصدر