Reacción #1904045

Ecuación de reacción

carbazole

p-dibromobenzene

sodium t-butoxide

o-xylene

→

9-(4-bromophenyl)carbazole

Rendimiento 44.4%

Disolventes

hexane toluene

Hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed
2. 2
   FiltraciónThe reaction mixture was filtered
3. 3
   Otroto remove insoluble matter
4. 4
   Lavadothe filter was washed with toluene and tetrahydrofuran successively
5. 5
   LavadoThe filtrate and wash liquid
6. 6
   Otrocondensed under reduced pressure
7. 7
   Temperaturaby heating
8. 8
   workup.STIRRINGstirring
9. 9
   Otroinsoluble matter was removed by filtration
10. 10
    Otrodried
11. 11
    workup.ADDITIONHexane was added to the residue
12. 12
    Filtraciónwas filtered off
13. 13
    Otrocondensed
14. 14
    Otrorecrystallized with hexane

Procedimiento

4.30 g (25.7 mmole) of carbazole, 18.19 g (77.1 mmole) of p-dibromobenzene, 0.14 g of palladium acetate and 0.33 g of 1,1′-bisdiphenyl phosphinoferrocene, 3.46 g of (36.0 mmole) sodium t-butoxide and 43 ml o-xylene were put in a 200 ml three-necked flask, and refluxed under stirring for 15 hours and 30 minutes under argon flow. The reaction mixture was filtered using a filter packed with alumina to remove insoluble matter, the filter was washed with toluene and tetrahydrofuran successively. The filtrate and wash liquid were combined and condensed under reduced pressure. Hexane was added to the residue, followed by heating and stirring, then insoluble matter was removed by filtration, and the filtrate was vacuum dried. Hexane was added to the residue and deposited crystal was filtered off. The filtrate was condensed, and refined by silica gel column chromatography (eluent:hexane/toluene:3/1), recrystallized with hexane to give 3.68 g of a white crystal of 9-(4-bromophenyl)carbazole (yield: 44.4%).

Fuente