Extracurricular laboratory: Synthetic route of 6065-82-3

Adding a certain compound to certain chemical reactions, such as: 6065-82-3, name is Ethyl diethoxyacetate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6065-82-3, Product Details of 6065-82-3

Adding a certain compound to certain chemical reactions, such as: 6065-82-3, name is Ethyl diethoxyacetate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6065-82-3, Product Details of 6065-82-3

Nine reactions were carried out in parallel and combined for work-up. A solution of 32 1-bromo-3,5-difluorobenzene (100 g, 518 mmol) in 15 THF (700 mL) was degassed and purged with 33 nitrogen three times. Then 2 M 34 LDA (311 mL) was added at -70 C. and the reaction mixture was stirred at -70 C. for 0.5 h under nitrogen. A solution of 35 ethyl 2,2-diethoxyacetate (96 g, 544 mmol) in THF (200 mL) was added drop-wise at -70 C. under nitrogen and the reaction mixture was stirred for 1 h. The reactions were combined and poured into ice saturated 36 ammonium chloride (10 L) in portions and extracted with EtOAc (3×3 L). The organic layer was separated, washed with brine (5 L), dried over sodium sulfate, concentrated, and purified by silica gel chromatography (eluted with petroleum ether EtOAc 1:0-100:1) to give the 37 title compound (1.26 kg, 84% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.12 (d, J=7.2 Hz, 2H), 5.15 (s, 1H), 3.61-3.7 (m, 4H), 1.2 (t, J=7.2 Hz, 6H).

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Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FATHEREE, PAUL R.; JIANG, LAN; MCKINNELL, ROBERT MURRAY; THALLADI, VENKAT R.; ZHANG, HAO; DABROS, MARTA; NZEREM, JERRY; BENJAMIN, NOAH; KLEINSCHEK, MELANIE A.; CRATER, GLENN D.; (40 pag.)US2018/311255; (2018); A1;,
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