451. Bromination of 2-nitro-p-cresol

WO Kermack, WT Spragg

Index: Kermack; Spragg Journal of the Chemical Society, 1932 , p. 2946

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Abstract

When nitrated, 3-bromo-p-cresol (111) yields 5-bromo-3-nitrop-cresol but, as shown above, its carbonate yields the carbonate of 5-bromo-2-nitro-p-cresol (compare p-cresol and its carbonate, which are nitrated in position 3 and 2 respectively). The bromine atom in compounds (I) and (11) and their derivatives is relatively inactive. For instance, 5-bromo-2- nitro-p-tolyl acetate, when treated in boiling acetic anhydride with sodium acetate and a ...