تفاعل #44631

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

الإجراء التجريبي

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:

المصدر