In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 23062-51-3 as follows. Quality Control of Methyl 4-bromobicyclo[2.2.2]octane-1-carboxylate
Intermediate A51E: Methyl 4-phenylbicyclo[2.2.2]octane-1-carboxylate To a suspension of aluminum trichloride (809 mg, 6.07 mmol) in benzene (4 mL, 1.214 mmol) at -10 C. was added a solution of Intermediate A51D (300 mg, 1.214 mmol) in benzene (2 mL) under nitrogen. The reaction mixture was gradually warmed up to RT and stirred overnight. It was carefully poured into ice water, extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated to afford Intermediate A51E (250 mg, 84%) as a tan solid, which was used for the next step without further purification. MS(ES): m/z=245 [M+H]+; 1H NMR (400 MHz, chloroform-d) delta ppm 7.42-7.29 (m, 4H), 7.29-7.16 (m, 1H), 3.77-3.65 (s, 3H), 2.07-1.80 (m, 1H).
According to the analysis of related databases, 23062-51-3, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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