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Preparation of Substituted Methyl o-Nitrophenyl Sulfides

Author(s): Katerina Dudova | Frantisek Castek | Vladimir Machacek | Petr Simunek

Journal: Molecules ISSN 1420-3049
Volume: 7; Issue: 1; Start page: 7; Date: 2002;
Original page

Keywords: Nucleophilic aromatic substitution | sulfur nucleophiles | ring closure

ABSTRACT
The nucleophilic substitution of substituted o-nitrochlorobenzenes with substituted methanethiolates, catalysed with triethylamine or pyridine, has been used to prepare a series of appropriately substituted methyl-o-nitrophenylsulfides. The prepared compounds were identified by their 1H- and 13C-NMR spectra. The base catalysed ring closure of methyl 2-(methoxycarbonylmethylsulfanyl)-3,5-dinitrobenzenecarboxylate only results in an attack of carbanion on the ester group, not on a nitro group as with the other compounds prepared. The cyclisation product is methyl 3-hydroxy-5,7-dinitrobenzo[b]thiophene-2-carboxylate (11).