Tetrahedron Letters, volume 44, issue 19, pages 3759-3761

Synthesis of 4-methoxy-3,5-dinitrobenzaldehyde: a correction to supposed tele nucleophilic aromatic substitution

Publication type: Journal Article
Publication date: 2003-05-01
scimago Q3
wos Q3
SJR: 0.323
CiteScore: 3.5
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
1,3-Dinitro-5-trichloromethylbenzene (2) was reacted with sodium methoxide in an attempt to prepare 4-methoxy-3,5-dinitrobenzaldehyde (7) via a reported tele nucleophilic aromatic substitution. The product from this reaction was methyl 3,5-dinitrobenzoate (5) and not the methoxy aldehyde as had been reported. The desired product was prepared by conventional nitration methodology from 4-methoxy-3-nitrobenzaldehyde.
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