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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 24
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Original Articles

Solvent-free nitration of electron-rich arenes

Bhumasamudram JagadishDepartment of Chemistry and Biochemistry, University of Arizona, Tucson, Arizona, USAView further author information
,
Nathaniel R. HurleyDepartment of Chemistry and Biochemistry, University of Arizona, Tucson, Arizona, USAView further author information
&
Eugene A. MashDepartment of Chemistry and Biochemistry, University of Arizona, Tucson, Arizona, USACorrespondence[email protected]
View further author information
Pages 2395-2398 | Received 21 Jun 2017, Published online: 30 Nov 2017
 
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ABSTRACT

Nitration of relatively electron-rich arenes does not require an additive or a solvent. For example, reaction on a gram scale of anisole with acetyl nitrate, generated in situ by mixing 100% HNO3 with acetic anhydride, produced 2,4-dinitroanisole in 82% yield after crystallization of the crude product. Results with five additional monosubstituted benzene derivatives possessing highly activated, weakly activated, or weakly deactivated rings are reported.

GRAPHICAL ABSTRACT

Additional information

Funding

This work was supported by the Strategic Environmental Research and Development Program [Grant number ER-2221].

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