Electric Literature of 19936-14-2, 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 19936-14-2 as follows.
A mixture of 5,5,5′,5′-tetramethyl-2,2′-bi(1,3,2-dioxaborinane) (16.50 g, 48.33 mmol), oven dried potassium acetate (20.03 g, 204.1 mmol), and 1-(4-bromophenyl)cyclobutanol (10.00 g, 44.03 mmol) in 1,4-dioxane (120 mL) was degassed with N2 for 15 min, then treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (2.44 g, 2.99 mmol). The reaction mixture was heated to 110 C. and stirred for 2 hours under N2. The reaction mixture was cooled to room temperature and filtered through celite, eluting with EtOAc. The filtrate was evaporated to give a black oil, which was purified by flash chromatography (0-50% EtOAc/Heptane) three times to afford the title compound (8.68 g, 76%) as a white solid. GC/MS: 259. 1H NMR (400 MHz, CD3Cl) delta 7.83 (d, J=8.05 Hz, 2H), 7.50 (d, J=8.29 Hz, 2H), 3.78 (s, 4H), 2.65-2.52 (m, 2H), 2.38-2.42 (m, 2H), 1.98-2.03 (m, 1H), 1.72-1.80 (m, 1H), 1.03 (s, 6H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19936-14-2, its application will become more common.
Reference:
Patent; PFIZER INC.; Bhattacharya, Samit; Cameron, Kimberly; Dowling, Matthew; Fernando, Dilinie; Ebner, David; Filipski, Kevin; Kung, Daniel; Lee, Esther; Smith, Aaron; Tu, Meihua; US2013/267493; (2013); A1;,
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