Zincke nitration

Zincke nitration
Named after Theodor Zincke
Reaction type Substitution reaction
Identifiers
RSC ontology ID RXNO:0000413

The Zincke nitration is an organic reaction in which a bromine substituent of a phenol or cresol is replaced by a nitro group by treatment with nitrous acid or sodium nitrite.[1] The reaction is a manifestation of nucleophilic aromatic substitution. The reaction is named after Theodor Zincke.

Two examples:[2]

and:[3]

The Zincke nitration should not be confused with the Zincke–Suhl reaction or the Zincke reaction.

References

  1. Zincke, Th., J. Prakt. Chem. 61, 561–567 (1900) and correction at J. Prakt. Chem. 63, 183 ff (1900).
  2. The Nitration of Brominated Fluorophenols by the Zincke Method L. Chas. Raiford and Arthur L. LeRosen J. Am. Chem. Soc.; 1944; 66(11) pp 1872–73; doi:10.1021/ja01239a020
  3. Behavior of Mixed Halogenated Phenols in the Zincke Method of Nitration L. Chas. Raiford and Glen R. Miller J. Am. Chem. Soc.; 1933; 55(5) pp 2125–31; doi:10.1021/ja01332a059
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