14348-41-5Relevant articles and documents
The Bromination of p-Hydroxybenzoic Acid in Aqueous Solution. Reaction via the Minor p-Carboxyphenoxide Anion Tautomer
Tee, Oswald S.,Iyengar, N. Rani,Kraus, Brigitte
, p. 973 - 976 (1985)
The kinetics of bromination of p-hydroxybenzoic acid have been measured in aqueous solution in the pH range 0-6.From the pH-log rate profile the reactive species appear to be the free acid (pH 5).However, the reactivity attributable to the monoanion is about 9 times higher than that predicted by a Hammett plot for the bromination of p-substituted phenols.This deviation is described to reaction via the tautomeric p-carboxyphenoxide monoanion which is present to the extent of 1 in 3100.Support for this proposal comes from related studies on ethyl p-hydroxybenzate, 3-bromo-4-hydroxybenzoic acid, and p-methoxybenzoic acid.In particular, the 3-bromo-4-hydroxybenzoate anion appears to be 5200 times more reactive than predicted and twice as reactive as the p-hydroxybenzoate anion.These anomalies are removed if reaction occurs via the minor tautomeric anion.
A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide
Wu, Yong-Qi,Lu, Hai-Jia,Zhao, Wen-Ting,Zhao, Hong-Yi,Lin, Zi-Yun,Zhang, Dong-Feng,Huang, Hai-Hong
supporting information, p. 813 - 822 (2020/02/15)
A convenient, rapid H2SO4-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H2SO4 using N-chlorosuccinimide and N-iodosuccinimide, respectively.
An efficient one pot method for synthesis of carboxylic acids from nitriles using recyclable ionic liquid [bmim]HSO4 Dedicated to my mentor Professor (Mrs.) Krishna Misra on her 76th birthday
Kumar, Satyanand,Dixit, Sandeep Kumar,Awasthi, Satish Kumar
supporting information, p. 3802 - 3804 (2014/07/07)
Environmentally benign ionic liquid [bmim]HSO4 was found suitable for conversion of nitriles into carboxylic acids under mild conditions with excellent purity.
Regioselective and high-yielding bromination of phenols and anilins using N-bromosaccharin and amberlyst-15
Baharfar,Alinezhad,Azimi,Salehian
experimental part, p. 863 - 865 (2012/04/23)
A regioselective and facile conversion method for bromination of anilines and phenols using N-bromosaccharine in the presence of a catalytic amount of Amberlyst-15 lead to enhancement of the reaction rate and yielded brominated products in good to excellent yields and short reaction times.