反応 #554601

反応方程式

dioxane

triphenylenyl trifluoromethanesulfonate

bis(pinacolato)diboron

potassium acetate

→

triphenylene-2-boronic acid

収率 51.9%

溶媒

water

反応条件

後処理

1. 1
   温度the resultant was refluxed
2. 2
   温度while heating for 8 hours
3. 3
   抽出followed by extraction with toluene
4. 4
   その他An aqueous phase was removed
5. 5
   洗浄an organic phase was washed with water and saturated brine
6. 6
   乾燥dried with magnesium sulfate
7. 7
   その他Magnesium sulfate was removed
8. 8
   workup.DISTILLATIONthe solvent was distilled under reduced pressure
9. 9
   その他The resulting residue was purified by means of silica gel column chromatography

実験手順

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.

出典