Reaktion #513562

Reaktionsgleichung

xylene

aniline

3-bromo-9-phenylcarbazole

sodium tert-butoxide

→

N-phenyl-(9-phenyl-9H-carbazol-3-yl)amine

Ausbeute 75.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis mixture was heated
2. 2
   Filtrationthis solution was filtered through Florisil, alumina, and celite
3. 3
   EinengenThe obtained filtrate was concentrated
4. 4
   workup.ADDITIONhexane and ethyl acetate were added to the residue, which
5. 5
   Sonstigewas followed by irradiation with ultrasound
6. 6
   SonstigeA solid precipitated
7. 7
   Filtrationwas collected by suction filtration
8. 8
   Sonstigedried

Vorschrift

Into a 500 mL three-neck flask were added 19 g (60 mmol) of 3-bromo-9-phenylcarbazole, 340 mg (0.6 mmol) of bis(dibenzylideneacetone)palladium (0), 1.6 g (3.0 mmol) of 1,1-bis(diphenylphosphino)ferrocene, and 13 g (180 mmol) of sodium tert-butoxide, and the atmosphere in the flask was substituted with nitrogen. Thereafter, 110 mL of dehydrated xylene and 7.0 g (75 mmol) of aniline were added to the mixture. This mixture was heated and stirred for 7.5 hours at 90° C. After the reaction was completed, about 500 mL of hot toluene was added to the solution, and this solution was filtered through Florisil, alumina, and celite. The obtained filtrate was concentrated, and hexane and ethyl acetate were added to the residue, which was followed by irradiation with ultrasound. A solid precipitated was collected by suction filtration and dried to give 15 g (75% yield) of N-phenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA) as cream colored powder. By a nuclear magnetic resonance measurement (NMR), it was confirmed that this compound was N-phenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA).

Quelle