The use of NN-dimethylformamide as a solvent in the condensation of aromatic chloro-compounds with arylamines can lead to preferential replacement of the chloro-group by the dimethylamino-group. A similar exchange has not been observed with bromo- and iodo-compounds.
R. S. Asquith, W. M. Lord, A. T. Peters and F. Wallace, J. Chem. Soc. C, 1966, 95 DOI: 10.1039/J39660000095
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