A Method for Heteroaromatic Nitration Demonstrating Remarkable Thermal Stability

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• 作者：Gregory L. Beutner ; Lopa Desai ; Dayne Fanfair ; Paul Lobben ; Eric Anderson ; Simon W. Leung ; Martin D. Eastgate
• 刊名：Organic Process Research & Development
• 出版年：2014
• 出版时间：December 19, 2014
• 年：2014
• 卷：18
• 期：12
• 页码：1812-1820
• 全文大小：457K
• ISSN：1520-586X

文摘

Herein we report a novel heterogeneous pyrrole nitration that can be run on a large scale in batch mode. Activation of sodium nitrate by SO₃鈥損yridine in acetonitrile leads to the formation of an insoluble nitronium sulfate intermediate that effects a high-yielding reaction. These conditions allow for a safer and practical nitration reaction with unique thermal stability that appears to be a function of the low solubility of the proposed nitronium ion carrier. Mechanistic insights gained from reaction kinetics as well as ¹H and ¹⁵N NMR studies are presented to support this analysis.