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Synthesis 1996; 1996(4): 514-518
DOI: 10.1055/s-1996-4244
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Convenient Synthesis of Triarylamines via Ester-Mediated Nucleophilic Aromatic Substitution

Tetsutaro Hattori, Takashi Satoh, Sotaro Miyano*
  • *Department of Biochemistry and Engineering, Faculty of Engineering, Tohoku University, Aramaki-Aoba, Aoba-ku, Sendai 980-77, Japan, Fax +81(22)2177262; E-mail miyano@chewsz.che.tohoku.ac.jp
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Publication Date:
31 December 2000 (online)

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A convenient method for the preparation of arylamines via nucleophilic displacement of methoxy- and/or fluorobenzoates with lithium amides is presented. Treatment of 2,6-di-tert-butyl-4-methoxyphenyl-2- or 4-fluorobenzoate (2 or 7) with lithium diarylamides 3e-h in THF and/or THF/HMPA under mild conditions affords the 2- or 4-(diarylamino)benzoates 4e-h or 8g, h in good to excellent yields.

2- or 4-(Diarlylamino)benzoates are easily prepared via the SNAr reaction