Реакция #11838

Уравнение реакции

dibromodecane

sodium hydride

carbazole

→

N-(10-bromodecyl)-carbazole

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   ДругоеThen the mixture was transferred into a funnel from which it
2. 2
   Температураthe mixture was refluxed for 48 h
3. 3
   ТемператураAfter cooling
4. 4
   Фильтрацияit was filtered
5. 5
   workup.DISTILLATIONThe filtrate was distilled in order
6. 6
   Другоеto remove
7. 7
   workup.ADDITIONThe residue was diluted with water
8. 8
   Экстракцияextracted with CH2Cl2
9. 9
   ПромывкаThe organics was washed with brine
10. 10
    Сушкаdried over anhydrous MgSO4 overnight
11. 11
    ДругоеAfter removed the solvent
12. 12
    Другоеby rotary evaporator, it
13. 13
    Другоеwas purified by silica chromography
14. 14
    Другоеto give
15. 15
    Другое31.6 g (41%, yield, mp 38˜40° C.) white solid product

Методика

10 g (0.25 mol) sodium hydride (60%) was added in several portions into a solution of 30.6 g (0.20 mol) carbazole in 200 mL THF. Then the mixture was transferred into a funnel from which it was added dropwisely into a solution of 180 g (0.6 mol) dibromodecane in 500 mL THF at 70° C. and the mixture was refluxed for 48 h. After cooling, it was filtered. The filtrate was distilled in order to remove remaining dibromodecane. The residue was diluted with water and extracted with CH2Cl2. The organics was washed with brine and dried over anhydrous MgSO4 overnight. After removed the solvent by rotary evaporator, it was purified by silica chromography to give 31.6 g (41%, yield, mp 38˜40° C.) white solid product. 1H NMR (500 MHz, CDCl3), δ (ppm): 8.14 (2H, d), 7.51 (2H, d), 7.44 (2H, d), 7.26 (2H, d), 4.30 (2H, t), 3.41 (2H, t), 1.27˜1.90 (16H, m).

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