A NOVEL ROUTE TO META-AMINOBENZOTRIFLUORIDE

Article abstract of DOI:10.1016/S0022-1139(00)82070-9

Products patterns can be altered in reactions of m-nitrobenzotrichloride (VI) with (AHF)x.NH4F complex.Side-chain fluorination predominates under 'mild' conditions.In contrast, 'forcing' conditions effected unexpected in-situ fluorination-reduction to give m-aminobenzotrifluoride (V) in high yield (75percent) and purity (99.6percent).In-situ reduction is probably initiated by a combination of iron from the stainless steel autoclave and trace amounts of moisture.The transformation of (VI) to (V) represents another type of in-situ fluorination-reduction of nitroaromatics, e.g. nitrobenzene (VII) to p-fluoroaniline (VIII). o-Nitrobenzotrichloride (XI) degraded under 'forcing' conditions with (AHF)x.NH4F.