Reaktion #2508990

Reaktionsgleichung

1-Tosyloxy-3,6,9-trioxadecane

2,7-dibromofluorene

Sodium hydride

→

2,7-dibromo-9,9-bis(3,6,9-trioxadecyl)fluorene

Ausbeute 60.0%

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 5 hours
2. 2
   Temperaturto refluxed over night
3. 3
   Temperaturcooled down
4. 4
   workup.ADDITIONpoured
5. 5
   workup.DISTILLATIONinto distill water
6. 6
   Extraktionextracted with chloroform (2×100 mL)
7. 7
   WaschenThe combined organic solutions were washed with saturated NaCI solution (2×100 mL)
8. 8
   workup.DISTILLATIONdistilled water (1×100 mL)
9. 9
   Trocknendried over MgSO4
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    SonstigeCrude oil was further purified by column chromatography
12. 12
    SonstigeThe fraction at Rf=0.12 was collected
13. 13
    Einengenconcentrated
14. 14
    Sonstigeto give 5.7 product in 60% yield

Vorschrift

2,7-dibromofluorene (5.0 g, 15.4 mmol) was dissolved in dried THF solution (30 mL). Sodium hydride (1.0 g, 40 mmol) was added to the THF solution at room temperature and refluxed for 5 hours. 1-Tosyloxy-3,6,9-trioxadecane (11.8 g, 37 mmol) in 20 mL of dry THF was added drop-wise to the refluxed solution. The mixture was allowed to refluxed over night, then cooled down, poured into distill water and extracted with chloroform (2×100 mL). The combined organic solutions were washed with saturated NaCI solution (2×100 mL), distilled water (1×100 mL), dried over MgSO4, and concentrated under reduced pressure. Crude oil was further purified by column chromatography using hexane/ethyl acetate (50/50) as eluant. TLC (ethyl acetate/Hexane=1/1) Rf =0.12. The fraction at Rf=0.12 was collected and concentrated to give 5.7 product in 60% yield. 1H NMR (300 MHz, CDCl3), 2.34(t, 4H), 2.77(t, 4H), 3.10-3.60(m, 22H), 7.40-7.60(m, 6H).

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