The synthesis of 2,5-bis(bromomethyl)aniline - a nitrogen-containing PPV precursor- was attempted.  Benzylic bromination (NBS/BPO) of 2,5-dimethyl aniline (1)  was unsuccessful, maybe due to the nucleophilic nature of nitrogen.  To lower the reactivity of the amino group, 1  was protected upon reaction with acetic anhydride or trifluoroacetic anhydride to yield the corresponding acetamides 2a  , and 2b  . Benzilic bromination of 2a  was unsuccessful while that of 2 b  resulted in the formation of monobrominated trifluoroacetamides 3a  and 3b  .

Synthesis of a nitrogen-containing PPV precursor monomer

243rd National Meeting (2012)

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