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Reaction of Salicylic Acid with N‐Bromosuccinimide
Author(s) -
Chen ShuMin,
Yeh PingYuan
Publication year - 1964
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.196400013
Subject(s) - chemistry , salicylic acid , carbon tetrachloride , pyridine , halogenation , 1,4 dioxane , medicinal chemistry , organic chemistry , biochemistry
The reaction of equimolar amounts of NBS with salicylic acid in carbon tetrachloride was found to give tribromophenol, 4‐bromo‐ and 4,6‐(not 4,5)‐dibromo‐salicylic acids, while the same reaction carried out in dioxane yielded only tribromophenol and 4‐bromosalicylic acid and addition of pyridine into the reaction mixture (in dioxane) decreased the yields of the products. The fact that no 4,6‐dibromosalicylic acid could be produced in a dioxane medium is a strong evidence showing that the bromination in dioxane takes place through dioxane dibromide as the intermediate.