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20.2.1.3.2.1.1 Variation 1: Using Sodium Bromite

DOI: 10.1055/sos-SD-020-00065

Lin, S.; Yan, L.; Liu, P.Science of Synthesis, (200720118.

Although the oxidation of methyl ketones to carboxylic acids by the haloform procedure generally employs a halogen and sodium hydroxide, a variation on this method uses sodium bromite.[‌110‌] Thus, the reactions of methyl ketones with sodium bromite and sodium bromide in aqueous sodium hydroxide and subsequent acid treatment give carboxylic acids 69 and bromoform in good yields (Scheme 26). Moreover, sodium bromite is a stable, crystalline solid and hence it is easier to handle than liquid bromine or gaseous chlorine. In the oxidation sodium hypobromite is assumed to be the active brominating agent; it is produced by the reaction between sodium bromite and sodium bromide under the basic conditions.

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