Example 1: Synthesis of 2-(cyclohexylthio)isoindoline-1,3-dione
1,2-Dicyclohexyl disulfide (0.51 g, 2.21 mmol) was dissolved in anhydrous acetonitrile (20 mL) with N-bromophthalimide (0.50 g, 2.21 mmol) in a microwave reactor. The microwave irradiation reaction was carried out at 100 °C and 1 bar pressure for 10 min. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by fast column chromatography with the eluent of hexane/ethyl acetate (2:1, v/v) to afford the target compound 2-(cyclohexylsulfanyl)isoindoline-1,3-dione as a light yellow solid (0.29 g, 52% yield).
1H NMR (CDCl3) δ: 7.95-7.91 (2H, dd, 3JHH = 5.46 Hz, 4JHH = 3.07 Hz), 7.81-7.76 (2H, dd, 3JHH = 5.46 Hz, 4JHH = 3.07 Hz), 3.22-3.15 (1H, tt, 3JHH = 3.63 Hz, 10.88 Hz), 1.95-1.88 (2H, m), 1.84-1.75 (2H, m), 1.65-1.57 (1H, m), 1.43-1.33 (2H, m), 1.32-1.18 (3H, m).
