Реакция #1904045

Уравнение реакции

carbazole

p-dibromobenzene

sodium t-butoxide

o-xylene

→

9-(4-bromophenyl)carbazole

Выход 44.4%

Растворители

hexane toluene

Hexane

Условия реакции

Обработка

1. 1
   Температураrefluxed
2. 2
   ФильтрацияThe reaction mixture was filtered
3. 3
   Другоеto remove insoluble matter
4. 4
   Промывкаthe filter was washed with toluene and tetrahydrofuran successively
5. 5
   ПромывкаThe filtrate and wash liquid
6. 6
   Другоеcondensed under reduced pressure
7. 7
   Температураby heating
8. 8
   workup.STIRRINGstirring
9. 9
   Другоеinsoluble matter was removed by filtration
10. 10
    Другоеdried
11. 11
    workup.ADDITIONHexane was added to the residue
12. 12
    Фильтрацияwas filtered off
13. 13
    Другоеcondensed
14. 14
    Другоеrecrystallized with hexane

Методика

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%).

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