Electric Literature of 144267-96-9, A common heterocyclic compound, 144267-96-9, name is Ethyl 3,4-difluorobenzoate, molecular formula is C9H8F2O2, its 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.
A solution of the respective phenol and the benzoate derivative or, respectively, the carboxylic acid derivative of an aromatic 6-membered heterocycle having 1 or 2 N-atoms, as defined in connection with formula (I), or their substituted derivatives in an appropriate solvent, preferably a polar aprotic solvent, most preferably DMSO, and preferably under addition of anhydrous K2C03 , was stirred at a temperature between 80C and 120C depending on the substrate until the limiting reactant was fully converted. The reaction was guenched by addition of water, extracted with organic solvent (preferably Et20, EtOAc and DCM depending on the substrate). The combined organic layers were washed with sat. agueous NaCI solution, dried over Na2S04 and evaporated to dryness under reduced pressure. The crude product was purified by flash column chromatography to give the desired biarylether. (V138) General procedure A: Ethyl 3,4-difluorobenzoate (348 mg, 1.87 mmol, 1.00 eguiv), 4-(tert- butyOphenol (336 mg, 2.24 mmol, 1.20 eguiv) and K2C03 (388 mg, 2.80 mmol, 1.50 eguiv) in DMSO (2 ml_) were stirred at 100 C for 22 h. Purification by column chromatography (EtOAc/petroleum ether 1/40) gave the desired product as colourless oil (451 mg, 1.43 mmol, 76%); HRMS (ESI) m/z calcd. for C19H2203F+ [M+H]+ 317.1547, found: 317.1549; NMR (400 MHz, Chloroform-cO delta 7.85 (dd, J = 11.2, 2.0 Hz, 1H), 7.80 – 7.73 (m, 1H), 7.42 – 7.35 (m, 2H), 7.02 – 6.94 (m, 3H), 4.37 (q, J = 7.1 Hz, 2H), 1.39 (t, J = 7.1 Hz, 3H), 1.33 (s, 9H).
The synthetic route of 144267-96-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL); REINMUELLER, Viktoria; ZHU, Jieping; (56 pag.)WO2017/158190; (2017); A1;,
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