Treating 1,5-difluoro-2,4-dinitrobenzene (
1) with
N1-phenyl-5-(trifluoromethyl)benzene-1,2-diamine (
4) and
N,
N-diisopropylethylamine in EtOH at
ca. 0 °C for 4 h affords a mixture of
N1-(5-ethoxy-2,4-dinitrophenyl)-
N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (
5) (38%) and
N
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Treating 1,5-difluoro-2,4-dinitrobenzene (
1) with
N1-phenyl-5-(trifluoromethyl)benzene-1,2-diamine (
4) and
N,
N-diisopropylethylamine in EtOH at
ca. 0 °C for 4 h affords a mixture of
N1-(5-ethoxy-2,4-dinitrophenyl)-
N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (
5) (38%) and
N1-(5-fluoro-2,4-dinitrophenyl)-
N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (
6) (51%) that can be separated by chromatography. Repeating the reaction in dichloromethane led to the sole formation of
N1-(5-fluoro-2,4-dinitrophenyl)-
N2-phenyl-4-(trifluoromethyl)benzene-1,2-diamine (
6) in 96% yield.
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