Synthesis
The general procedure for the synthesis of 4-(4-trifluoromethylphenoxy)aniline from p-bromobenzotrifluoride was as follows: to a stirred solution of 4-bromobenzotrifluoride (11.2 g, 50 mmol) in dimethylsulfoxide (50 mL) was added powdered potassium carbonate (3.4 g, 60 mmol) and 4-aminophenol (6.6 g, 55 mmol) sequentially. The reaction suspension was heated and stirred at 90 °C for 4.5 hours. After completion of the reaction, the mixture was poured into water and extracted with diisopropyl ether. The organic phase was separated, filtered and decanted, and the organic phase was washed with water and subsequently dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 9.6 g of brown oily crude product. The crude product was ground with pentane, the precipitate was collected by filtration, washed with pentane and dried to give 3.3 g of the target compound 4-(4-trifluoromethylphenoxy)aniline in 27% yield with a melting point of 72 °C.
