Reacción #11840

Ecuación de reacción

N-(10-bromodecyl)-carbazole

2,7-dibromofluorene

sodium hydride

→

title product

Rendimiento 34.1%

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

Rendimiento 34.1%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwisely at 70° C.
2. 2
   Temperaturathe mixture was refluxed for 48 h
3. 3
   TemperaturaAfter cooling
4. 4
   Filtraciónthe solid was filtered
5. 5
   Concentraciónthe filtrate was concentrated
6. 6
   workup.ADDITIONdilute with water
7. 7
   Extracciónextracted with CH2Cl2
8. 8
   OtroThe organic layer was collected
9. 9
   Lavadowashed with brine
10. 10
    Secadodried with anhydrous MgSO4
11. 11
    OtroThe crude product was further purified by silica column chromography

Procedimiento

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.

Fuente