Reacción #554601

Ecuación de reacción

dioxane

triphenylenyl trifluoromethanesulfonate

bis(pinacolato)diboron

potassium acetate

→

triphenylene-2-boronic acid

Rendimiento 51.9%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resultant was refluxed
2. 2
   Temperaturawhile heating for 8 hours
3. 3
   Extracciónfollowed by extraction with toluene
4. 4
   OtroAn aqueous phase was removed
5. 5
   Lavadoan organic phase was washed with water and saturated brine
6. 6
   Secadodried with magnesium sulfate
7. 7
   OtroMagnesium sulfate was removed
8. 8
   workup.DISTILLATIONthe solvent was distilled under reduced pressure
9. 9
   OtroThe resulting residue was purified by means of silica gel column chromatography

Procedimiento

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.

Fuente