Synthesis
General procedure for the synthesis of 3-bromo-3-ethylpentane from 3-ethyl-3-pentanol: A mixture of alcohol (0.5 mmol) and halosilane (0.55 mmol), which had been electrically treated for 1-2 min, was transferred to a 4 mL screw-capped vial and stirred or heated at room temperature. The reaction mixture was maintained at 70-75 °C for 0.5 h to 24 h, during which the reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the crude reaction mixture was cooled to room temperature and the volatile product (TMS) 2O was removed by evaporation under reduced pressure at 30-35 °C and the residue was analyzed by 1H NMR. If necessary, the final product was purified by dry silica column chromatography. Detailed experimental information, including isolated yields, spectroscopic data, and other identification data, is provided in the Characterization Data for Isolated Final Products section of the Supporting Information (SI).
References
[1] Tetrahedron Letters, 2016, vol. 57, # 22, p. 2430 - 2433
[2] Bulletin of the Chemical Society of Japan, 1980, vol. 53, # 4, p. 1181 - 1182
[3] Tetrahedron Letters, 2003, vol. 44, # 41, p. 7589 - 7591
[4] Journal of the American Chemical Society, 1950, vol. 72, p. 2735
[5] Journal of the Institute of Petroleum, 1948, vol. 34, p. 350
