2,6-Dimethylaniline → 2,6-Dimethylaniline

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Reaction Steps

It is known that 4-bromo-2,6-dialkylanilines are predominantly formed by brominating 2,6-dialkylanilines. The high reactivity of these compounds causes the reaction to proceed non-selectively with the formation of different by-products, depending on the reaction conditions. Thus, for example, the bromination of 2,6-dimethylaniline in the presence of glacial acetic acid gives 4-bromo-2,6-dimethylaniline in a yield of 80-85% of theory (Chem. Ber. (1901), 34, 2242). The bromination of 2,6-dimethylaniline in strongly acid medium always results in the formation of substantial amounts of 3-bromo-2,6-dimethylaniline (Chem. Ber. (1900), 33, 1967). It is further known from published UK patent application A 2 098 210 that, in the halogenation of N-alkyl-2,6-dialkylanilines in the presence of a Lewis acid such as AlCl3, the halogen is even introduced selectively in 3-position.

Provenance & Evidence