Реакция #11839

Уравнение реакции

bromooctane

2,7-dibromofluorene

sodium hydride

→

solid

Выход 150.4%

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

Выход 150.4%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Температураrefluxed overnight
2. 2
   КонцентрированиеThe mixture was concentrated
3. 3
   workup.ADDITIONdiluted with water
4. 4
   Экстракцияextracted with diethyl ether
5. 5
   ПромывкаAfter washing with brine
6. 6
   Сушкаthe ether solution was dried over anhydrous MgSO4
7. 7
   Другоеthe ether was then removed by evaporation
8. 8
   ДругоеThis crude solid was purified by a silica chromography with hexane
9. 9
   Другоеrecrystallized from ethanol

Методика

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).

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