Reacción #11839

Ecuación de reacción

bromooctane

2,7-dibromofluorene

sodium hydride

→

solid

Rendimiento 150.4%

9,9-di-(n-octyl)-2,7-dibromofluorene

Rendimiento 150.4%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed overnight
2. 2
   ConcentraciónThe mixture was concentrated
3. 3
   workup.ADDITIONdiluted with water
4. 4
   Extracciónextracted with diethyl ether
5. 5
   LavadoAfter washing with brine
6. 6
   Secadothe ether solution was dried over anhydrous MgSO4
7. 7
   Otrothe ether was then removed by evaporation
8. 8
   OtroThis crude solid was purified by a silica chromography with hexane
9. 9
   Otrorecrystallized from ethanol

Procedimiento

To a solution of 28.5 g (88 mmol) 2,7-dibromofluorene in 800 mL THF was added 8.8 g (220 mmol) sodium hydride (60%) in several portions at room temperature. The mixture was heated at 60° C. and 43 g (220 mmol) bromooctane in 200 mL THF was added dropwisely into the mixture and refluxed overnight. The mixture was concentrated and diluted with water, and then extracted with diethyl ether. After washing with brine, the ether solution was dried over anhydrous MgSO4 and the ether was then removed by evaporation. This crude solid was purified by a silica chromography with hexane and recrystallized from ethanol to give white solid (36.3 g, yield 75.3%, mp. 52˜54° C.). 1H NMR (500 MHz, CDCl3), δ (ppm): 7.51 (2H, d), 7.44 (2H, d), 7.41 (2H, s), 1.89 (4H, m), 1.02˜1.20 (20H, m), 0.81 (6H, t), 0.56 (4H, m).

Fuente