Using 4-iodo-m- dimethylbenzene (1.43 mL, 10.0 mmol) and 2-aminothiophenol (1.07 mL, 10.0 mmol) as raw materials, the above raw materials were mixed with cuprous iodide (0.19 g, 1.0 mmol), potassium carbonate (6.90 g, 50.0 mmol) and dried and degassed dimethylsulfoxide (50 mL) under nitrogen protection at 120 °C for 16 h with stirring. After completion of the reaction, the mixture was cooled to room temperature, diluted with water (50 mL) and the product was extracted with ethyl acetate (2 x 150 mL). The organic layers were combined and washed sequentially with water (3 x 150 mL) and brine (3 x 150 mL). The organic phase was dried over anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure to afford 2-((2,4-dimethylphenyl)thio)aniline as a dark colored oil (2.15 g, 94% yield). The structure of the product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3, 500 MHz) and mass spectrometry (ESI): 1H NMR δ 2.28 (s, 3H), 2.40 (s, 3H), 4.24 (br s, 2H), 6.71 (d, J = 8.1 Hz, 1H), 6.75-6.81 (m, 2H), 6.87 (m, 1H) 7.02 (m, 1H), 7.23 (m, 1H), 7.38 (dd, J = 1.5, 7.7 Hz, 1H); MS (ESI) m/z: 230 [MH]+.
