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Updated: Jan 15, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Synthesis and crystal structure of (E)-N-[(2-bromo-phen-yl)methyl-idene]-3,5-bis-(tri-fluoro-meth-yl)aniline
Nicholas B Kingsley1, Tyler J Doyon2, Daron E Janzen3
1Department of Green Chemistry and Biochemistry, University of Michigan-Flint, 303 E. Kearsley St, Flint, MI 48502, USA.
Abstract:
The title compound C15H8BrF6N, was prepared by a condensation reaction of 2-bromo-benzaldehyde and 3,5-bis-(tri-fluoro-meth-yl)aniline in the presence of anhydrous magnesium sulfate. The compound readily crystallizes from a concentrated hexa-nes solution in high yield. The imine bond is nearly planar with the 2-bromo-phenyl group, while the N-(3,5-bis-(tri-fluoro-meth-yl)phenyl moiety is significantly twisted from the imine group [49.61 (5)°]. The crystal packing involves short inter-molecular C-H⋯Br contacts linking zigzag ribbons flanked by fluorous layers.
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