Cz. Dong et al., HALOGENATION OF SOME BENZAMIDES TAKES PLACE PREFERENTIALLY AT THE ORTHO,PARA POSITIONS, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (8), 1998, pp. 1689-1696
The orientation of chlorination and bromination of N,N-disubstituted b
enzamides in aqueous acetic acid is strongly influenced by the nature
of the alkyl groups at the nitrogen atom. With large groups, the halog
enation takes place fairly selectively at the ortho/para positions.