Zincke nitration

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., [2] 61, 563 (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 - 1873; 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 - 2131; doi:10.1021/ja01332a059