Réaction #11840

Équation de réaction

N-(10-bromodecyl)-carbazole

2,7-dibromofluorene

sodium hydride

→

title product

Rendement 34.1%

9,9-Bis(N-carbazolyl-decyl)-2,7-dibromofluorene

Rendement 34.1%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added dropwisely at 70° C.
2. 2
   Températurethe mixture was refluxed for 48 h
3. 3
   TempératureAfter cooling
4. 4
   Filtrationthe solid was filtered
5. 5
   Concentrationthe filtrate was concentrated
6. 6
   workup.ADDITIONdilute with water
7. 7
   Extractionextracted with CH2Cl2
8. 8
   AutreThe organic layer was collected
9. 9
   Lavagewashed with brine
10. 10
    Séchagedried with anhydrous MgSO4
11. 11
    AutreThe crude product was further purified by silica column chromography

Mode opératoire

To a mixture of 5.2 g (16 mmol) 2,7-dibromofluorene in 300 mL THF was added 1.3 g (41 mmol) sodium hydride (75%) in several portions. A mixture of 15 g (39 mol) N-(10-bromodecyl)-carbazole (8) in 100 mL THF was added dropwisely at 70° C. and the mixture was refluxed for 48 h. After cooling, the solid was filtered and the filtrate was concentrated and dilute with water and extracted with CH2Cl2. The organic layer was collected and washed with brine and dried with anhydrous MgSO4. The crude product was further purified by silica column chromography to give 5.1 g (yield 34%, mp 94˜96° C.) title product. 1H NMR (CDCl3), δ (ppm): 8.10 (4H, d), 7.38˜7.48 (14H, m), 7.23 (4H, t), 4.27 (4H, t), 0.88˜1.86 (36H, m). Anal. Calcd: C, 73.22; H, 6.68; N, 3.00. Found: C, 72.58; H, 6.59; N, 2.73.

Source