Zincke nitration

What is Zincke nitration?

The Zincke nitration is a chemical reaction that involves replacing ortho– or para-bromine or iodine atoms in phenols with a nitro group upon treatment with nitrous acid, HNO2, or a nitrite in acetic acid. It is worth noting that this reaction cannot be used with fluorine or chlorine atoms, as shown in the accompanying figure.

Zincke nitration - nitrous acid HNO2 - nitrite in acetic acid
Zincke nitration

References

Zincke, T. (1900), Ueber die Einwirkung von salpetriger Säure auf Brom- und Chlorderivate von Phenolen. [On the effect of nitrous acid on bromine and chlorine derivatives of phenols.] J. Prakt. Chem., 61: 561-567. https://doi.org/10.1002/prac.19000610145

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