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Zincke Nitration

(Zincke Method)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr698

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Zincke Nitration. Comprehensive Organic Name Reactions and Reagents. 698:3168–3171.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The replacement method of hydrogen, bromine or iodine atom at the ortho- or para-position with respect to a hydroxyl group of halophenol or halocresol with a nitro group by means of treatment with nitrous acid or a nitrite in acetic acid is generally referred to as the Zincke method or Zincke nitration. Under these standard conditions, only bromo and iodo groups are replaced by a nitro group, although chloro and fluoro groups can also be substituted under special conditions. It has been reported that phenols with two strong activating groups that also function as directing groups, the Zincke nitration does not proceed smoothly; however, when the hydroxyl group is protected by an acyl group (e.g., acetyl, benzoyl), the aromatic nucleus can be nitrated by fuming nitric acid. Several examples of nitration particularly for the phenols and 2,4,6-tribromo-m-cresol have been discussed. This reaction has been used for the preparation of nitrophenols.

Keywords:

  • halophenols;
  • nitrophenols;
  • hydroxyl group;
  • 2,4-dibromo-6-nitro-m-cresol