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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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化学
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JoVE 杂志 化学
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

DOI:
10.3791/53789-v

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08:43 min

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January 19, 2016

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,
1Department of Chemistry,State University of New York at Stony Brook, 2Institute of Chemical Biology and Drug Discovery,State University of New York at Stony Brook

Chapters

  • 00:05Title
  • 00:53Precursor Preparation: Synthesis of Methyl 4-(N-hydroxyacetamido) Benzoate
  • 04:33Synthesis of Methyl 4-(N-trifluoromethoxy)acetamido) Benzoate
  • 05:58Synthesis of Methyl 4-Acetamido-3-(trifluoromethoxy) Benzoate via Trifluoromethoxy-migration
  • 07:14Results: Synthesis of Trifluoromethoxylated Aniline Derivatives Using Togni Reagent II
  • 08:12Conclusion

Summary

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An operationally simple procedure for the synthesis of ortho-trifluoromethoxylated aniline derivatives via a two-step sequence of O-trifluoromethylation of N-aryl-N-hydroxyacetamide followed by thermally induced intramolecular OCF3-migration is reported.

Tags

Ortho-trifluoromethoxylated AnilineAniline DerivativesReductionHydrogenationAcetyl ProtectionRhodium CatalystCelite FiltrationTLC MonitoringAnhydrous SolventsNitrogen Atmosphere

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