Reaction #554601

Reaction equation

dioxane

triphenylenyl trifluoromethanesulfonate

bis(pinacolato)diboron

potassium acetate

→

triphenylene-2-boronic acid

Yield 51.9%

Solvents

water

Conditions

Workup

1. 1
   Temperaturethe resultant was refluxed
2. 2
   Temperaturewhile heating for 8 hours
3. 3
   Extractionfollowed by extraction with toluene
4. 4
   OtherAn aqueous phase was removed
5. 5
   Washan organic phase was washed with water and saturated brine
6. 6
   Dryingdried with magnesium sulfate
7. 7
   OtherMagnesium sulfate was removed
8. 8
   workup.DISTILLATIONthe solvent was distilled under reduced pressure
9. 9
   OtherThe resulting residue was purified by means of silica gel column chromatography

Procedure

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.

Source