Reaktion #1448923

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 mixture was filtered through Florisil, alumina, and celite
3. 3
   SonstigeAn oily substance was obtained by concentration of the filtrate, and hexane and ethyl acetate
4. 4
   workup.ADDITIONwere added to the substance, 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 by 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 at 90° C. for 7.5 hours under nitrogen. After the reaction was completed, about 500 mL of hot toluene was added to the reacted mixture, and this mixture was filtered through Florisil, alumina, and celite. An oily substance was obtained by concentration of the filtrate, and hexane and ethyl acetate were added to the substance, 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,9-diphenyl-9H-carbazol-3-amine (abbreviation: PCA).

Quelle