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Published TCIMAIL newest issue No.201
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TCI Practical Example: Chlorination Using Chlorotrimethylsilane
We are proud to present the direct chlorination of 3-ethyl-3-pentanol using chlorotrimethylsilane.
Procedure
A mixture of 3-ethyl-3-pentanol (20.0 g, 172 mmol) and chlorotrimethylsilane (20.6 g, 189 mmol) was stirred at 70 °C for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the volatile byproduct was removed under reduced pressure. The residue was distilled at atmospheric pressure (130 °C) to afford 3-chloro-3-ethylpentane (15.0 g, 65% yield) as a clear colorless liquid.
Experimenter’s Comments
The reaction was monitored by 1H NMR.
Analytical Data
3-Chloro-3-ethylpentane
1H NMR (400 MHz, CDCl3); δ 1.78 (q, J = 7.3 Hz, 6H), 0.96 (t, J = 7.3 Hz, 9H).
Lead Reference
- Direct halogenation of alcohols with halosilanes under catalyst- and organic solvent-free reaction conditions
