Réaction #1904045

Équation de réaction

carbazole

p-dibromobenzene

sodium t-butoxide

o-xylene

→

9-(4-bromophenyl)carbazole

Rendement 44.4%

Solvants

hexane toluene

Hexane

Conditions de réaction

Traitement

1. 1
   Températurerefluxed
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Autreto remove insoluble matter
4. 4
   Lavagethe filter was washed with toluene and tetrahydrofuran successively
5. 5
   LavageThe filtrate and wash liquid
6. 6
   Autrecondensed under reduced pressure
7. 7
   Températureby heating
8. 8
   workup.STIRRINGstirring
9. 9
   Autreinsoluble matter was removed by filtration
10. 10
    Autredried
11. 11
    workup.ADDITIONHexane was added to the residue
12. 12
    Filtrationwas filtered off
13. 13
    Autrecondensed
14. 14
    Autrerecrystallized with hexane

Mode opératoire

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%).

Source