Oxidative bromination of vanillin

VL Afanas' eva, AV Lyubeshkin, SS Kovaleva…

Index: Afanas'eva, V. L.; Lyubeshkin, A. V.; Kovaleva, S. S.; Bagreeva, M. R.; Anisimova, O. S.; Glushkov, R. G. Pharmaceutical Chemistry Journal, 1987 , vol. 21, # 11 p. 805 - 809 Khimiko-Farmatsevticheskii Zhurnal, 1987 , vol. 21, # 11 p. 1367 - 1371

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Abstract

One of the most effective methods for obtaining 3,4,5-trimethoxybenzaldehyde -- an essential intermediate in the preparation of 2,4-diamino-5-(3,4,5-trimethoxybenzyl) pyrimi- dine (trimethoprim) -- is a three-stage synthesis based on vanillin (I), which includes bromi- nation of I in glacial acetic acid to 5-bromovanillin (II), replacement of bromine by a methoxy group, and methylation of the syringaldehyde formed [8]. This method for brominating I, as well ...