Roscales García, SilviaGarcía Csaky, Aurelio2025-12-162025-12-162019-07-17Silvia Roscales and Aurelio G. Csákÿ .Journal of Chemical Education, 2019 96 (8): 1738-1744 DOI: 10.1021/acs.jchemed.8b0082410.1021/acs.jchemed.8b00824https://hdl.handle.net/20.500.14352/129110A method for the synthesis of flufenamic acid, a nonstereoidal anti-inflammatory drug (NSAID) of the anthranilate family (fenams), is described as an experiment for the upper-division undergraduate organic chemistry laboratory. The key step is the formation of the diarylamine moiety of flufenamic acid by a novel reaction consisting of the coupling of nitrosobenzenes with boronic acids under transition-metal-free conditions. On the one hand, students can compare the performance of two different methods for the preparation of nitrosobenzenes (oxidation of amines and ipso-SEAr reaction on potassium organotrifluoroborates). On the other hand, they compare the yields of two complementary examples for the coupling of nitrosobenzenes with boronic acids. The reactions are followed by thin layer chromatography, and the products are purified by percolation or by column chromatography. Students are also tasked with the confirmation of the structure of the products based on melting point, infrared, 1 H NMR, 13C NMR, and 19F NMR spectroscopy, and MS spectrometryengjournal articleopen access54Upper-Division Undergraduate,Organic ChemistryCollaborative/Cooperative LearningAromatic CompoundsDrugs/PharmaceuticalsNonmetalsQuímica23 Química