Реакция #554601

Уравнение реакции

dioxane

triphenylenyl trifluoromethanesulfonate

bis(pinacolato)diboron

potassium acetate

→

triphenylene-2-boronic acid

Выход 51.9%

Растворители

water

Условия реакции

Обработка

1. 1
   Температураthe resultant was refluxed
2. 2
   Температураwhile heating for 8 hours
3. 3
   Экстракцияfollowed by extraction with toluene
4. 4
   ДругоеAn aqueous phase was removed
5. 5
   Промывкаan organic phase was washed with water and saturated brine
6. 6
   Сушкаdried with magnesium sulfate
7. 7
   ДругоеMagnesium sulfate was removed
8. 8
   workup.DISTILLATIONthe solvent was distilled under reduced pressure
9. 9
   ДругоеThe resulting residue was purified by means of silica gel column chromatography

Методика

Under an argon atmosphere, 37.6 g of triphenylenyl trifluoromethanesulfonate, 27.9 g of bis(pinacolato)diboron, 2.45 g of 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride dichloromethane complex, 1.66 g of 1,1′-bis(diphenylphosphino)ferrocene and 29.4 g of potassium acetate were placed in a flask. 600 mL of anhydrous dioxane was added thereto, and the resultant was refluxed with stirring while heating for 8 hours. After cooling to room temperature, 300 mL of water was added to the reaction solution, followed by extraction with toluene. An aqueous phase was removed, and an organic phase was washed with water and saturated brine, and then dried with magnesium sulfate. Magnesium sulfate was removed and the solvent was distilled under reduced pressure. The resulting residue was purified by means of silica gel column chromatography, whereby 14.1 g (yield: 40%) of triphenylene-2-boronic acid picohal ester was obtained.

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