Reaktion #1435686

Reaktionsgleichung

magnesium

TEOS

1,4-dibromobenzene

iodine

→

1,4-bis(triethoxysilyl)benzene

Ausbeute 43.0%

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewere placed under nitrogen in a 1 L three-neck round bottom flask
2. 2
   Sonstigeequipped with magnetic stir bar, condenser, and addition funnel
3. 3
   Temperaturto reflux
4. 4
   workup.ADDITIONthe addition
5. 5
   Temperaturat reflux for 1 h
6. 6
   Sonstigewas removed in vacuo
7. 7
   workup.ADDITIONHexane (200 mL) was added
8. 8
   Sonstigeto precipitate any remaining magnesium salts in solution
9. 9
   Filtrationthe mixture was quickly filtered under nitrogen
10. 10
    Sonstigeto produce a clear, light brown solution
11. 11
    SonstigeHexane was removed in vacuo
12. 12
    workup.DISTILLATIONThe product was purified by fractional distillation
13. 13
    SonstigeThe product was recovered as a clear liquid at 130–5° C. (0.2 mmHg) in 43–47% yield

Vorschrift

A mixture of magnesium turnings (15 g) and TEOS (450 mL, 2 mol) in THF (300 mL) were placed under nitrogen in a 1 L three-neck round bottom flask equipped with magnetic stir bar, condenser, and addition funnel. A small crystal of iodine was added and the mixture was brought to reflux. A solution of 1,4-dibromobenzene (48 g, 204 mmol) in THF (100 mL) was added dropwise over 2 h. Within 30 min of initiating the addition, the reaction became mildly exothermic. The reaction mixture was kept at reflux for 1 h after the completion of the addition of dibromide. The gray-green mixture was allowed to cool to room temperature before the THF was removed in vacuo. Hexane (200 mL) was added to precipitate any remaining magnesium salts in solution and the mixture was quickly filtered under nitrogen to produce a clear, light brown solution. Hexane was removed in vacuo. The product was purified by fractional distillation. The product was recovered as a clear liquid at 130–5° C. (0.2 mmHg) in 43–47% yield. 1H NMR (500 MHz, CDCl3) δ 7.67 (s, 4H, ArH), 3.86 (q, J=7.00 Hz, 12H, OCH2CH3), 1.23 (t, J=7.00 Hz, 18H, ArH); 13C NMR (125 MHz, CDCl3) δ 133.25,57.98, 17.43; 29Si NMR (99 MHz, CDCl3) δ−58.25; MS m/e calc'd for CI (M) C18H34Si2O6: 402.1894, found 402.1886.

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