1552-17-6

1635-61-6

108-95-2

1552-17-6

General steps: 1. Dissolve 2-nitro-5-chloroaniline (6 mmol), phenol (6 mmol) and potassium carbonate (9 mmol or 18 mmol, as appropriate) in dimethylsulfoxide (25 mL) and stir the reaction at 80 °C. The reaction time varied depending on the product: 5a required 5 h, 5b and 5d required 4 h, 5c required 4.35 h, and 5f required 8 h. The reaction was carried out at 80 °C. The reaction time varied depending on the product. After completion of the reaction, the mixture was cooled, poured into water, the precipitate was collected by filtration, dried and recrystallized from alcohol to give the target product 2-nitro-5-phenoxyaniline. 2. Alternative method: 2-nitro-5-chloroaniline (6 mmol), phenol (6 mmol) or the corresponding phenol (3 mmol) and potassium carbonate (9 mmol or 18 mmol, as appropriate) are dissolved in dimethylsulfoxide (25 mL) and subjected to sonication at 80°C. The reaction time varies depending on the product. The reaction time varied depending on the product: 1 h for 3a, b and 5a-d, 6 h for 5e and 2 h for 3c and 5f. After completion of the reaction, the mixture was cooled, poured into water, the precipitate was collected by filtration, dried and recrystallized from alcohol to give the target product 2-nitro-5-phenoxyaniline.