Convenient Synthesis of Triarylamines via Ester-Mediated Nucleophilic Aromatic Substitution

Tetsutaro Hattori; Takashi Satoh; Sotaro Miyano

doi:10.1055/s-1996-4244

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

Abstract

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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 S_NAr reaction

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