Reacción #11838

Ecuación de reacción

dibromodecane

sodium hydride

carbazole

→

N-(10-bromodecyl)-carbazole

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThen the mixture was transferred into a funnel from which it
2. 2
   Temperaturathe mixture was refluxed for 48 h
3. 3
   TemperaturaAfter cooling
4. 4
   Filtraciónit was filtered
5. 5
   workup.DISTILLATIONThe filtrate was distilled in order
6. 6
   Otroto remove
7. 7
   workup.ADDITIONThe residue was diluted with water
8. 8
   Extracciónextracted with CH2Cl2
9. 9
   LavadoThe organics was washed with brine
10. 10
    Secadodried over anhydrous MgSO4 overnight
11. 11
    OtroAfter removed the solvent
12. 12
    Otroby rotary evaporator, it
13. 13
    Otrowas purified by silica chromography
14. 14
    Otroto give
15. 15
    Otro31.6 g (41%, yield, mp 38˜40° C.) white solid product

Procedimiento

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).

Fuente