반응 #1904045

반응 방정식

carbazole

p-dibromobenzene

sodium t-butoxide

o-xylene

→

9-(4-bromophenyl)carbazole

수율 44.4%

용매

hexane toluene

Hexane

반응 조건

후처리

1. 1
   온도refluxed
2. 2
   여과The reaction mixture was filtered
3. 3
   기타to remove insoluble matter
4. 4
   세척the filter was washed with toluene and tetrahydrofuran successively
5. 5
   세척The filtrate and wash liquid
6. 6
   기타condensed under reduced pressure
7. 7
   온도by heating
8. 8
   workup.STIRRINGstirring
9. 9
   기타insoluble matter was removed by filtration
10. 10
    기타dried
11. 11
    workup.ADDITIONHexane was added to the residue
12. 12
    여과was filtered off
13. 13
    기타condensed
14. 14
    기타recrystallized with hexane

실험 절차

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%).

출처