Visible-light-induced radical bromination of ethyl 6-methyl-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate (1) was effectively conducted with N-bromosuccinimide using a 150-W tungsten bulb as an initiator, leading to the desired monobromo product ethyl 6-(bromomethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate (2) in good yield of 76 %. Using the present procedure, a 46 % improvement in yield of 2 was achieved when compared with the previous method used by us. In addition, the trace amount of byproduct was isolated and identified as ethyl 9-bromo-6-methyl-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate (3) based on 1H nuclear magnetic resonance (NMR) spectral analysis. As an extended application of 2, a new synthesis of symmetrical 2-quinolylmethoxyphenyl-containing diethers 11a–c was achieved via Williamson reaction with some dihydroxy arenes (10a–c).
Research on Chemical Intermediates – Springer Journals
Published: Mar 19, 2014
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