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Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
N-(3-Bromo-1,4-dioxo-1,4-dihydro-2-naphth-yl)-4-fluoro-N-(4-fluoro-benzo-yl)benzamide
Emmanuel S Akinboye1, Ray J Butcher, Dwayne A Wright
1Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA.
Abstract:
In the title compound, C(24)H(12)BrF(2)NO(4), synthesized from 2-amino-3-bromo-1,4-naphthoquinone and 4-fluoro-benzoyl chloride, the two p-fluoro-phenyl rings are inclined at 73.9 (1) and 73.6 (1)° to the naphthoquinone ring system. The two imido carbonyl O atoms are anti to each other, while the fluoro-phenyl rings are located opposite each other, connected to the imide group in a funnel-like arrangement. This conformation allows the fluorine groups be oriented slightly away from each other. An examination of the packing shows a close inter-molecular F⋯O contact of 2.982 (5) Å and a Br⋯O contact of 2.977 (4) Å. In addition, the mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯F inter-actions.
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