Chemical Properties
2-CYCLOHEXYLETHYL BROMIDE is colourless to yellow liquid
Uses
2-CYCLOHEXYLETHYL BROMIDE is a reagent used in the cross-coupling and Grignard reactions. It is used in the synthesis of immunosuppressive agents consisting of 5-phenylalkoxypsoralens as well as agon ists for human vitamin-D resistant Rickets.
Uses
1-Bromo-2-cyclohexylethane may be used in the synthesis of 2-cyclohexylethyloxy-4-nitroaniline.
General Description
1-Bromo-2-cyclohexylethane is a halogenated hydrocarbon. Reaction of 1-bromo-2-cyclohexylethane with pillar[5]arene has been investigated.
Synthesis
General procedure for the synthesis of 2-cyclohexylethane bromoethane from 2-cyclohexylethanol: In a 1-liter round-bottomed flask fitted with a reflux condenser, 88.7 g (0.693 mol) of 2-cyclohexylethanol was added, followed by the slow addition of 164 g of concentrated sulfuric acid and 200 g of hydrobromic acid (48% aqueous), cooled in an ice bath. The reaction mixture was heated to reflux for 6 hours. After completion of the reaction, it was cooled to room temperature and the reaction was quenched by the addition of 400 g of ice. The aqueous phase was extracted with 400 ml of pentane and the organic layers were combined. The organic layer was washed sequentially with 2M NaOH solution and water and then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure and the product was finally purified by vacuum distillation to give 112.7 g (85% yield) of 2-cyclohexylethyl bromide as a colorless oil.1H-NMR (400 MHz, CDCl3): δ= 3.40 (2H, t, CH2Br), 1.73-1.61 (m, 7H), 1.44 (m, 1H), 1.26-1.11 ( m, 3H), 0.92-0.84 (m, 2H) ppm.
References
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 6, p. 1693 - 1703
[2] Patent: US8299287, 2012, B2. Location in patent: Page/Page column 43
[3] Patent: JP6196581, 2017, B2. Location in patent: Paragraph 0156
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 12, p. 2253 - 2260
[5] Bulletin de la Societe Chimique de France, 1948, p. 586,588
