Bromination of a water or acetic acid solution of methyl-2-acetylaminophenyl ketone gives a nuclear substitution product ; with dry material or in the presence of concentrated sulfuric acid, halogen enters the side chain, Baeyer and Bloem [Ber., 17, 963 (1884)]. With methyl-4-acetylaminophenyl ketone it has been found in this laboratory that the highest yield of nuclear bromide is obtained by allowing 1.84 molecular proportions of bromine, dissolved in 19.8 volumes of glacial acetic acid to drop during a period of twenty minutes into a solution containing one molecular proportion of the ketone dissolved in 20 times its weight of 50% acetic acid, while the mixture is shaken and the temperature kept at 20-21 ° , and the whole allowed to stand for 3¾ hours. When water is not present, substitution usually takes place in the side chain. This work has been done in order to identify products obtained in the study of the condensation reactions of methyl-4-aminophenyl ketone.
Proceedings of the Iowa Academy of Science
©1925 Iowa Academy of Science, Inc.
Raiford, L. Chas. and Davis, H. L.
"Bromination of Methyl-4-Acetylaminophenyl Ketone,"
Proceedings of the Iowa Academy of Science, 32(1), 324-324.
Available at: https://scholarworks.uni.edu/pias/vol32/iss1/46