Synthesis
Example 1 (Preparation of 1,3,5-tris(4-iodophenyl)benzene): 116 g of 1,3,5-triphenylbenzene, 19 mL of concentrated sulfuric acid (as a catalyst), and 1520 mL of 80% acetic acid (as a reaction solvent) were sequentially added to a 2L three-necked flask. The reaction mixture was heated to 70 °C under stirring conditions. Subsequently, 143 g of iodine and 69.3 g of periodate were added in batches over a period of about 2.5 hours (Note: in the original text, "n-stereo acid" should be "periodate"). After the addition, the reaction was continued with stirring for 6 hours, during which a white precipitate was generated. At the end of the reaction, toluene was added to the reaction mixture to dissolve the precipitate and separate the toluene layer from the water layer. The toluene layer was washed with aqueous sodium bicarbonate and aqueous sodium thiosulfate in turn. The washed organic layer was concentrated and purified by silica gel column chromatography, and finally recrystallized with ethanol/toluene mixed solvent to obtain 34.6 g of the target product 1,3,5-tris(4-iodophenyl)benzene as white needle-like crystals in 13.3% yield.
