Synthesis
Example 18 Preparation of 4-(2-iodoethyl)octylbenzene: In a 1 liter single neck round bottom flask fitted with a calcium chloride protective tube, 4-octylbenzene ethyl methanesulfonate (70 g) and anhydrous tetrahydrofuran (500 mL) were added and covered with a light-avoiding black protective cover. The mixture was stirred for 10 minutes and then sodium iodide (133 g) was added and stirring was continued overnight at room temperature. Upon completion of the reaction, the solvent was removed by vacuum evaporation. The residue was dissolved in water (300 mL) and extracted with ethyl acetate (2 x 250 mL). The ethyl acetate extracts were combined, washed sequentially with aqueous sodium thiosulfate and dried over sodium sulfate, and finally the target product 4-(2-iodoethyl)octylbenzene was obtained by vacuum concentration. Yield: 70 g.
References
[1] Journal of Organic Chemistry, 2004, vol. 69, # 11, p. 3950 - 3952
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 15, p. 2946 - 2961
[3] Patent: US2014/235895, 2014, A1. Location in patent: Paragraph 0255
[4] Patent: WO2015/92809, 2015, A2. Location in patent: Page/Page column 9
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 20, p. 4605 - 4616
