Electric Literature of 1647-26-3,Some common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, molecular formula is C8H15Br, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Into a flask under an inert atmosphere of N2, were placed magnesium (0.4 g, 16.25 mmol) and iodine (0.02 g, 0.072mmol) in THF (5 mL), then (2-bromoethyl)cyclohexane (2.1 g, 10.83 mmol) in THF (10 mL) was added dropwise at 80 C and the reaction was stirred for 1.5 h, then cooled to RT. Into another flask under an inert atmosphere of N2, was placed zinc (II) bromide (2.4 g, 10.83 mmol) in THF (35 mL), followed by the dropwise addition of the Grignard reagent (preparedabove) at 0 C. The mixture was stirred at RT for 1 h, then bis(triphenylphosphine)palladium chloride (0.5 g, 0.72 mmol) and 6,8-dibromoimidazo[1,2-a]pyrazine (2 g, 7.22 mmol) were added and stirred at RT for 1.5 h. The reaction was quenched by the addition of sat. aq. NH4C1 (50 mL) and extracted with EtOAc (3 x 50 mL). The combined organic layer was washed with brine (2 x 100 mL), dried over anhydr. Na2SO4, filtered, concentrated to drynessin vacuo, and the residue purified by column chromatography with EtOAc/petroleum ether (10-45%) to afford the title compound.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-cyclohexylethane, its application will become more common.
Reference:
Patent; MERCK SHARP & DOHME CORP.; WHITEHEAD, Alan; ORNOSKI, Olga; RAGHAVAN, Subharekha; BERGER, Raphaelle; GARFUNKLE, Joie; YANG, Zhiqiang; JI, Gang; JIANG, Falong; FU, Jianmin; (132 pag.)WO2017/197555; (2017); A1;,
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