Synthesis of 4-methoxy-3,5-dinitrobenzaldehyde: A correction to supposed tele nucleophilic aromatic substitution
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. © 2003 Elsevier Science Ltd. All rights reserved.
Monk, K., Siles, R., Pinney, K., & Garner, C. (2003). Synthesis of 4-methoxy-3,5-dinitrobenzaldehyde: A correction to supposed tele nucleophilic aromatic substitution. Tetrahedron Letters, 44 (19), 3759-3761. https://doi.org/10.1016/S0040-4039(03)00751-2