(4 - vinyl phenyl) dimethyl silane synthesis
- Product Name:(4 - vinyl phenyl) dimethyl silane
- CAS Number:4556-72-3
- Molecular formula:C10H14Si
- Molecular Weight:162.3
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Yield:4556-72-3 80%
Reaction Conditions:
Stage #1: 1-bromo-4-ethenyl-benzenewith n-butyllithium in tetrahydrofuran;hexane at -78; for 2.5 h;
Stage #2: Chlorodimethylsilan in tetrahydrofuran;hexane at -78 - 20; for 8 h;
Steps:
Dimethyl(4-vinylphenyl)silane (Compound 1n)
Dimethyl(4-vinylphenyl)silane (Compound 1n)
In a 100 mL round-bottom flask, 1-bromo-4-vinylbenzene (1.83 g, 10.0 mmol) in THF (15 mL) was cooled to -78° C. n-BuLi (7.5 mL, 1.6 M in hexane) was added dropwise very slowly over 30 minutes.
The resulting mixture was stirred at -78° C. for 2 hours before the dropwise addition of a solution of chlorodimethylsilane (1.1 mL, 10.0 mmol) in THF (20 mL).
The reaction was allowed to warm to room temperature and stirred for 8 hours.
The reaction mixture was quenched with NH4Cl (5 mL, sat. aq.) and the product was extracted with Et2O (15 mL*3).
The organic layer was washed with water (20 mL), then brine (20 mL), then dried over MgSO4 and concentrated under reduced pressure (200 torr).
The crude product was purified by silica column chromatography with pentane to afford In (1.29 g, 7.95 mmol, 80%).
This compound is known (136).
1H NMR (400 MHz, CDCl3) δ 7.51 (d, J=8.1 Hz, 2H), 7.41 (d, J=7.9 Hz, 2H), 6.72 (dd, J=17.6, 10.9 Hz, 1H), 5.79 (dd, J=17.6, 0.9 Hz, 1H), 5.27 (dd, J=10.9, 0.9 Hz, 1H), 4.43 (hept, J=3.7 Hz, 1H), 0.35 (d, J=3.8 Hz, 6H).
References:
US2017/218346,2017,A1 Location in patent:Paragraph 0270; 0271
