Mild electrophilic halogenation of chloropyridines using CCl4 or C2Cl6 under basic phase transfer conditions

Ashutosh V. Joshi, Mubeen Baidossi, Nida Qafisheh, Elsa Chachashvili, Yoel Sasson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Effective chlorination of 2,3,5,6-tetrachloropyridine to pentachloropyridine was realized under mild phase transfer conditions with carbon tetrachloride and 50% NaOH or solid K3PO4. Mechanistic study of this reaction indicated the possibility of an aromatic carbanionic intermediate. Hexachloroethane was established as a more selective electrophilic chlorination agent.

Original languageEnglish
Pages (from-to)5061-5063
Number of pages3
JournalTetrahedron Letters
Volume45
Issue number26
DOIs
StatePublished - 21 Jun 2004

Keywords

  • Aromatic carbanion
  • Halogenation
  • Phase transfer
  • Polyhalomethane
  • Potassium phosphate

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