Reaktion #1904045

Reaktionsgleichung

carbazole

p-dibromobenzene

sodium t-butoxide

o-xylene

→

9-(4-bromophenyl)carbazole

Ausbeute 44.4%

Lösungsmittel

hexane toluene

Hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Sonstigeto remove insoluble matter
4. 4
   Waschenthe filter was washed with toluene and tetrahydrofuran successively
5. 5
   WaschenThe filtrate and wash liquid
6. 6
   Sonstigecondensed under reduced pressure
7. 7
   Temperaturby heating
8. 8
   workup.STIRRINGstirring
9. 9
   Sonstigeinsoluble matter was removed by filtration
10. 10
    Sonstigedried
11. 11
    workup.ADDITIONHexane was added to the residue
12. 12
    Filtrationwas filtered off
13. 13
    Sonstigecondensed
14. 14
    Sonstigerecrystallized with hexane

Vorschrift

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%).

Quelle