Reacción #1265003

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 solution was filtered through Florisil, alumina, and celite
3. 3
   ConcentraciónThe obtained filtrate was concentrated
4. 4
   workup.ADDITIONhexane and ethyl acetate were added to the residue, 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 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 gieve 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).

Fuente