Reacción #1448923

Ecuación de reacción

xylene

aniline

3-bromo-9-phenylcarbazole

sodium-tert-butoxide

→

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

Rendimiento 75.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThis mixture was heated
2. 2
   Filtraciónthis mixture was filtered through Florisil, alumina, and celite
3. 3
   OtroAn 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
   Otrowas followed by irradiation with ultrasound
6. 6
   OtroA solid precipitated
7. 7
   Filtraciónwas collected by suction filtration
8. 8
   Otrodried

Procedimiento

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).

Fuente