32337-83-0Relevant academic research and scientific papers
Experimental and Theoretical Investigations of the Bromination of Phenols with β and γ Aliphatic Substituents, including Rings
Zhang, Jinsong,Chang, Xiao,Bowman, Erich C.,Holt, Carter J.,Lodewyk, Michael W.,Miller, Randy M.,Xia, Guangming
, p. 9292 - 9296 (2015/09/28)
Bromination reactions of substituted and ring fused phenols were studied by both experiment (t-BuNH-Br) and computation (density functional theory). The outcomes support each other, indicating a clear and predictable regioselective preference among 3,4-bis-alkylated and 3,4-ring-fused phenols.
ipso Halogenation. II. Bromination of phenols, isomerisation and disproportionation of bromophenols, and dione-phenol rearrangement of bromodienones
Fischer, Alfred,Henderson, George Narayanan
, p. 1045 - 1052 (2007/10/02)
Bromination of p-cresol, bromo-p-cresol, 3,4-dimethylphenol, and mesitol in trifluoromethanesulfonic acid gices as the main product the bromo derivative with bromine meta to hydroxyl, a result attributed to the intermediate formation of a bromodienone and its rearrangement.Phenols does not give m-bromophenol in trifluoromethanesulfonic acid. 4-Bromo-2,4,6-trimethylcyclohexa-2,5-dienone rearranges to 3-bromomesitol in trifluoromethanesulfonic acid and, similarly, 2,4,6-tribromo-4-methylcyclohexa-2,5-dienone rearranges to 3-bromomesitol in trifluoromethanesulfonic acid and, similarly, 2,4,6-tribromo-4-methylcyclohexa-2,5-dienone rearranges to 2,3,6-tribromo-4-methylphenol.Under appropriate conditions debromination of bromodienones is competitive with rearrangement.Tetramethylammonium bromide in trifluoromethanesulfonic acid is an effective reagent for isomerization and disproportionation of bromophenols.Tetramethylammonium iodide in trifluoromethanesulfonic acid is an effective reagent for selective debromination of bromophenols at the ortho and para position.
