반응 #11839

반응 방정식

bromooctane

2,7-dibromofluorene

sodium hydride

→

solid

수율 150.4%

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

수율 150.4%

용매

THF

THF

반응 조건

후처리

1. 1
   온도refluxed overnight
2. 2
   농축The mixture was concentrated
3. 3
   workup.ADDITIONdiluted with water
4. 4
   추출extracted with diethyl ether
5. 5
   세척After washing with brine
6. 6
   건조the ether solution was dried over anhydrous MgSO4
7. 7
   기타the ether was then removed by evaporation
8. 8
   기타This crude solid was purified by a silica chromography with hexane
9. 9
   기타recrystallized from ethanol

실험 절차

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).

출처