Category: 19936-14-2

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.

To a solution of 5.66 g of 1-(4-bromophenyl)-cyclobutanol (24.92 mmol, described in example S2-A) in 70 ml DCM were added 4.23 g of (diethylamino)sulfur trifluoride (95%, 24.92 mmol) at 0 C. The reaction mixture was stirred at 0 C. for 35 min, then sat. NaHCO3- solution was added and the resulting mixture was extracted with DCM. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give a residue which was purified by flash column chromatography (100% pentane) to give 1-bromo-4-(1-fluoro-cyclobutyl)-benzene (3.66 g, 64%) as a colorless liquid.

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; Conte, Aurelia; Kuehne, Holger; Luebbers, Thomas; Mattei, Patrizio; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2007/185058; (2007); A1;,
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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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Synthetic Route of 19936-14-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 19936-14-2, name is 1-(4-Bromophenyl)cyclobutanol. This compound has unique chemical properties. The synthetic route is as follows.

To a 50 mL two-neck flask were added 1-(4-bromophenyl)cyclobutanol (80 mg, 0.35 mmol), N-(1-((1-cyanocyclopropyl)carbamoyl)cyclohexyl)-6-(4,4,5,5 -tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-2-carboxamide (168.0 mg, 0.35 mmol), Pd(dppf)Cl2¡¤CH2Cl2 (40 mg) and DMF (15 mL). To the mixture was added aqueous potassium carbonate (0.45 mL, 2 mol/L) under nitrogen protection. The resulting mixture was stirred at 90C for 3 h. To the reaction mixture was added saturated brine (50 mL), and the resulting mixture was extracted with ethyl acetate (50 mL*2). The combined organic layers were washed with saturated brine (40 mL*2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica-gel column chromatography (DCM:EtOAc=4:1, V/V) to give a white solid (80 mg, 50%). MS(ESI, pos.ion)m/z:498.2 (M+1); 1H NMR (600 MHz, CDCl3) delta 8.16 (s, 1H), 7.77 (d, J= 10.6 Hz, 2H), 7.67 (dd, J= 20.5, 8.3 Hz, 4H), 7.61 (d, J = 8.2 Hz, 1H), 7.54 (s, 1H), 6.61 (s, 1H), 2.69 – 2.61 (m, 2H), 2.45 (dt, J = 12.5, 9.5 Hz, 2H), 2.28 (d, J = 13.8 Hz, 2H), 2.15 – 1.98 (m, 5H), 1.82 – 1.72 (m, 4H), 1.55 (dt, J = 24.7, 9.6 Hz, 4H), 1.26 – 1.23 (m, 2H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 19936-14-2, 1-(4-Bromophenyl)cyclobutanol.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; WANG, Xiaojun; ZHOU, Pingjian; YANG, Chuanwen; HUANG, Changwei; XIONG, Shaohui; ZHANG, Yingjun; ZHANG, Jiancun; (139 pag.)EP3342765; (2018); A1;,
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