Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 27, Pages 5323-5330Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100571
Keywords
Halogenation; Nitrogen heterocycles; Electrophilic substitution; Nucleophilic substitution
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Funding
- National High Technology Research and Development Program (863 Program) of China [2009AA032901]
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A novel, straightforward, and highly regioselective 4-chlorination of 3-oxypyrazole derivatives in boiling thionyl chloride (SOCl2) in the presence of catalytic N,N-dimethylformamide (DMF) has been developed. This reaction likely proceeds through a DMF-catalyzed electrophilic/nucleophilic chlorination mechanism and involves electrophilic attack by SOCl2 and nucleophilic substitution by Cl- as the key steps. Based on this mechanism, the corresponding 4-bromination and 4-iodination of 3-oxypyrazoles have also been achieved in good yield by adding Br- and I-, respectively, to the reaction system. This halogenation method enables quick access to many original 4-halo-3-oxypyrazole series.
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