Abstract
A number of 2-.carbethoxy-3-methylbenzofuran derivatives were synthesized. A 5,5-gem-dibromo derivative was obtained in the bromination of 2-carbethoxy-3-methyl-4-oxo-4, 5,6,7,tetrahydrobenzofuran. Dehydrobromination of this, dibromo derivative gave 2-carbethoxy-3-methyl-4-hydroxy-5-bromobenzofuran. Depending on the structure of the starting compound and the brominating agent, the bromine in the bromination of 2-carbethoxy-3-methyl-4-hydroxy- and 4-acetoxybenzofurans with bromine and N-bromosuccinimide is incorporated either in the methyl group or in 5 and 7 positions of the benzofuran ring. The nitration of 2-carbethoxy-3-methyl-4-hydroxybenzofuran and its bromo derivative leads to 5-nitro- and 5,7-dinitrobenzofuran derivatives. The structures of the synthesized benzofuran derivatives were established by means of the PMR spectra.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 27–29, January, 1980.
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Grinev, A.N., Lyubchanskaya, V.M. & Uretskaya, G.Y. Synthesis of 2-carbethoxy-3-methyl-4-hydroxybenzofuran derivatives. Chem Heterocycl Compd 16, 20–22 (1980). https://doi.org/10.1007/BF00475383
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DOI: https://doi.org/10.1007/BF00475383