Nitrogen → 4-(4-Fluorophenoxy)-1-methyl-2-nitrobenzene

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4-Bromo-2-nitrotoluene (25.0 g, 116 mmol), 4-fluorophenol (8.70 g, 77.6 mmol), potassium carbonate (21.5 g, 156 mmol) and pyridine (75 mL), were combined under N2 atmosphere and heated at 90° C. for 30 min. The reaction mixture was cooled to ambient temperature, CuO (15.4 g, 194 mmol) was added under a stream of N2, and the resulting dark-brown suspension was heated at reflux for 17 hours. The reaction mixture was cooled to ambient temperature and diluted with ether. The solids were removed by filtration through celite. The ethereal solution was washed with 1.0M aqueous NaOH, 1.0M aqueous HCl and brine, dried over Na2SO4, filtered and concentrated in vacuo to give a dark-brown oil. The crude product was purified by chromatography on silica gel to give 2-nitro-4-(4-fluorophenoxy)-toluene (12.1 g, 63%).

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