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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.

Used Chemicals

• Chlorotrimethylsilane (= TMSCl) [C0306]
• 3-Ethyl-3-pentanol [E0157]

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
  • N. Ajvazi, S. Stavber, Tetrahedron Lett. 2016, 57, 2430.