Reaktion #11839

Reaktionsgleichung

bromooctane

2,7-dibromofluorene

sodium hydride

→

solid

Ausbeute 150.4%

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

Ausbeute 150.4%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed overnight
2. 2
   EinengenThe mixture was concentrated
3. 3
   workup.ADDITIONdiluted with water
4. 4
   Extraktionextracted with diethyl ether
5. 5
   WaschenAfter washing with brine
6. 6
   Trocknenthe ether solution was dried over anhydrous MgSO4
7. 7
   Sonstigethe ether was then removed by evaporation
8. 8
   SonstigeThis crude solid was purified by a silica chromography with hexane
9. 9
   Sonstigerecrystallized from ethanol

Vorschrift

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).

Quelle