반응 #554601

반응 방정식

dioxane

triphenylenyl trifluoromethanesulfonate

bis(pinacolato)diboron

potassium acetate

→

triphenylene-2-boronic acid

수율 51.9%

용매

water

반응 조건

후처리

1. 1
   온도the resultant was refluxed
2. 2
   온도while heating for 8 hours
3. 3
   추출followed by extraction with toluene
4. 4
   기타An aqueous phase was removed
5. 5
   세척an organic phase was washed with water and saturated brine
6. 6
   건조dried with magnesium sulfate
7. 7
   기타Magnesium sulfate was removed
8. 8
   workup.DISTILLATIONthe solvent was distilled under reduced pressure
9. 9
   기타The resulting residue was purified by means of silica gel column chromatography

실험 절차

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.

출처