preparation | 3, 5-diiodo-4-hydroxybenzaldehyde is prepared as follows: 4-hydroxybenzaldehyde (1.0g,8.19mmol), sodium periodate (1.75g,8.19mmol) and NaCl(957mg,16.38mmol) are dissolved in acetic acid (30mL) in a 100mL round bottom flask. H2O(3mL) was added at room temperature. The reaction mixture was stirred at room temperature for 10 minutes, then potassium iodide (2.72g,16.4mmol) was added and the reaction mixture was stirred at room temperature for 96 hours. The reaction mixture was diluted with EtOAc(25mL) and 1M sodium thiosulfate aqueous solution. Add the solution (25mL) and stir the resulting mixture for 15 minutes. The solution was poured into 250mLErlenmeyer and washed with EtOAc(50mL) and 1M sodium thiosulfate aqueous solution. Solution (50mL) and stir the resulting solution for another 15 minutes. The organic layers were separated and the aqueous phase was further extracted with EtOAc(3 × 50mL). The combined organic layers were washed with brine (100mL), dried with Na2SO4, filtered and concentrated to dry to give 4-hydroxy-3, 5-diiodobenzaldehyde (2.91g,95% yield) as a light yellow solid. |