R. Blasco, Carmen Ramírez de Arellano, J. F. Sanz-Cervera
May 4, 2017
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Influential Citations
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Organic Preparations and Procedures International
Abstract
The monohalogenation products of 3-hydroxybenzaldehyde (1) are useful synthons for the preparation of more complex molecules. For example, the introduction of a halogen allows the use of a Suzuki-type coupling for the preparation of substituted biphenyls. However, monohalogenated derivatives of 1 have been the subject of a certain amount of controversy in the past, with several papers incorrectly assigning the chemical structures of the regioisomers isolated. For example, while Pandya et al. reported a method for the direct bromination of 1 to afford 4-bromo-3-hydroxybenzaldehyde (3) under acidic conditions in 1952, Barfknecht et al. later determined that the product obtained under these conditions was actually 2-bromo-5-hydroxybenzaldehyde 2 (Scheme 1).