Synthesis
GENERAL STEPS: To a solution of 1,2-dimethylbenzene (0.106 g, 1 mmol) in acetonitrile (10 mL) was sequentially added iodine (1 mmol, 0.126 g) and polymer-loaded periodate (0.6 g, 1.05 mmol). The reaction mixture was stirred at 40 °C for 1 hour. The progress of the reaction was monitored by thin layer chromatography (TLC) and the unfolding agent was a solvent mixture of ethyl acetate and hexane (1:9, v/v). After completion of the reaction, the mixture was cooled to room temperature and filtered. Excess iodine in the filtrate was quenched by adding sodium bisulfite solution (1 M) dropwise. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography, eluting with a mixed solvent gradient of hexane and ethyl acetate to give 1-ethyl-4-iodobenzene in 95% isolated yield with a boiling point of 235 °C (literature value: 234 °C).
References
[1] Bulletin of the Chemical Society of Ethiopia, 2014, vol. 28, # 2, p. 305 - 308
[2] Journal of applied chemistry of the USSR, 1984, vol. 57, # 1 pt 2, p. 121 - 123
[3] Journal fuer Praktische Chemie (Leipzig), 1902, vol. <2> 65, p. 568
[4] Journal of the Indian Chemical Society, 1936, vol. 13, p. 187
[5] Journal of the Indian Chemical Society, 1937, vol. 14, p. 157
