Convenient synthesis of pure fluorous alkyl azides at multigram scale

Máté Berta, András Dancsó, Anikó Nemes, Zoltán Pathó, D. Szabó, J. Rábai

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The reaction of F-alkylation reagents including (perfluoroalkyl)alkyl halides and sulfonates [Rfn(CH2)mX (X=Br, I, OTs, OTf)], and a slight excess of NaN3 in DMSO at 100°C for 5h, followed by steam distillation, allowed the isolation of azides Rfn(CH2)mN3 in good to excellent yields with high purity (GC assay ≥98%). Due to the stability of these fluorous azides they can be distilled at atmospheric or lower pressures for further purification. 4-Azidoperfluorotoluene (p-CF3C6F4N3) and 1-azidooctane were also prepared under similar conditions starting from perfluorotoluene (CF3C6F5) or 1-iodooctane, respectively. Steam distillation allowed easy and safe product isolations up to 50g scale.

Original languageEnglish
JournalJournal of Fluorine Chemistry
DOIs
Publication statusAccepted/In press - Jun 20 2016

    Fingerprint

Keywords

  • Fluorous
  • Organic azides
  • Steam-distillation

ASJC Scopus subject areas

  • Environmental Chemistry
  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this