Synthesis
In a round-bottom flask equipped with a stir bar, add 1 equivalent of 3-iodoxetine, 1.2 equivalents of triphenylphosphine, and 1.2 equivalents of imidazole. Empty the flask and reintroduce N2 three times. Add 0.1 M dichloromethane to the mixture and cool the reaction mixture to 0°C using an ice-water bath. Then, add 1.2 equivalents of iodine to the mixture in portions. Remove the ice-water bath and stir the reaction mixture at room temperature for 16 hours. After the reaction is complete, dilute the reaction mixture with 30 mL of H2O, separate the layers, and extract the aqueous layer with CH2Cl2 (3 × 30 mL). Wash the combined organic layers with 30 mL of saturated Na2S2O3 and 30 mL of brine. Dry the combined organic layers on MgSO4 and filter. Concentrate the filtrate under vacuum and purify the residue by silica gel column chromatography to obtain the product.
