反応 #1904045

反応方程式

carbazole

p-dibromobenzene

sodium t-butoxide

o-xylene

→

9-(4-bromophenyl)carbazole

収率 44.4%

溶媒

hexane toluene

Hexane

反応条件

後処理

1. 1
   温度refluxed
2. 2
   ろ過The reaction mixture was filtered
3. 3
   その他to remove insoluble matter
4. 4
   洗浄the filter was washed with toluene and tetrahydrofuran successively
5. 5
   洗浄The filtrate and wash liquid
6. 6
   その他condensed under reduced pressure
7. 7
   温度by heating
8. 8
   workup.STIRRINGstirring
9. 9
   その他insoluble matter was removed by filtration
10. 10
    その他dried
11. 11
    workup.ADDITIONHexane was added to the residue
12. 12
    ろ過was filtered off
13. 13
    その他condensed
14. 14
    その他recrystallized with hexane

実験手順

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%).

出典