Preparation
3-Methlisoquinoline (0.05 g, 0.35 mmol), iodine (0.09 g, 0.35 mmol), iodic acid (0.02 g, 0.12 mmol), and water (3 mL) were added together and heated at reflux for 6 hours. After the reaction mixture cooled, it was extracted and washed three times with dichloromethane. The organic layers were washed with a saturated sodium thiosulfate solution until the color went from deep purple to light yellow. The organic layers were collected, combined, and dried with sodium sulfate. The resulting solution was evaporated to a solid. The product was then purified via flash chromatography to isolate 4-iodo-3-methylisoquinoline (average yield: 30-40%) and the structure was confirmed via GC-MS and NMR.
