To a Silak reaction tube equipped with a magnetic stirrer were sequentially added 6.2 mg of silver sulfate (Ag2SO4), 36.3 mg of copper acetate (Cu(OAc)2), 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline (as a ligand), 36.2 mg of 5-methyl-2-nitrobenzoic acid (as a substrate) and 17.5 mg of sodium chloride (NaCl) in 4 mL of dimethyl sulfoxide (DMSO). The reaction mixture was heated and stirred in an oil bath at 160 °C for 24 h under oxygen (O2) atmosphere. Upon completion of the reaction, the reaction was quenched by the addition of an appropriate amount of distilled water, followed by three extractions with ethyl acetate (10 mL each). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 14.8 mg of 3-chloro-4-nitrotoluene (target product) in 43% yield.
