Synthesis
Under nitrogen protection, cyclohexanemethanol (5.00 mL, 40.7 mmol) was dissolved in dichloromethane (101 mL) and cooled to 0 °C. Imidazole (3.6 g, 52.9 mmol), triphenylphosphine (13.9 g, 52.9 mmol) and iodine (13.4 g, 52.9 mmol) were added sequentially and the reaction mixture was stirred for 30 minutes. After completion of the reaction, dichloromethane was added to the reaction solution. The organic layer was washed sequentially with water and aqueous sodium thiosulfate, and the organic layer was dried with anhydrous sodium sulfate and subsequently concentrated. The concentrate was filtered through diatomaceous earth to further concentrate the filtrate. Finally, the crude product obtained was purified by silica gel column chromatography (80 g of silica gel, pentane as eluent) to give the colorless oily product (iodomethyl)cyclohexane (5.82 g, 64% yield).
References
[1] Patent: JP2017/119691, 2017, A. Location in patent: Paragraph 0179
[2] Chemische Berichte, 1907, vol. 40, p. 4865
[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906, vol. 142, p. 344
[4] Bulletin de la Societe Chimique de France, 1906, vol. <3> 35, p. 548
