Réaction #11838

Équation de réaction

dibromodecane

sodium hydride

carbazole

→

N-(10-bromodecyl)-carbazole

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   AutreThen the mixture was transferred into a funnel from which it
2. 2
   Températurethe mixture was refluxed for 48 h
3. 3
   TempératureAfter cooling
4. 4
   Filtrationit was filtered
5. 5
   workup.DISTILLATIONThe filtrate was distilled in order
6. 6
   Autreto remove
7. 7
   workup.ADDITIONThe residue was diluted with water
8. 8
   Extractionextracted with CH2Cl2
9. 9
   LavageThe organics was washed with brine
10. 10
    Séchagedried over anhydrous MgSO4 overnight
11. 11
    AutreAfter removed the solvent
12. 12
    Autreby rotary evaporator, it
13. 13
    Autrewas purified by silica chromography
14. 14
    Autreto give
15. 15
    Autre31.6 g (41%, yield, mp 38˜40° C.) white solid product

Mode opératoire

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).

Source