反应 #1435686

反应方程式

magnesium

TEOS

1,4-dibromobenzene

iodine

→

1,4-bis(triethoxysilyl)benzene

收率 43.0%

溶剂

THF

THF

THF

反应条件

后处理

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

实验过程

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.

来源