Analyzing the synthesis route of 1-(2,6-Difluorophenyl)ethanol

Statistics shows that 87327-65-9 is playing an increasingly important role. we look forward to future research findings about 1-(2,6-Difluorophenyl)ethanol.

Related Products of 87327-65-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.87327-65-9, name is 1-(2,6-Difluorophenyl)ethanol, molecular formula is C8H8F2O, molecular weight is 158.15, as common compound, the synthetic route is as follows.

Example 35A rac-Ethyl 8-[1-(2,6-difluorophenyl)ethoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate 5.50 g (23.5 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate Example 20A together with 4.46 g (28.2 mmol) of 1-(2,6-difluorophenyl)ethanol, 5.35 ml (27.0 mmol) of diisopropyl azodicarboxylate and 7.08 g (27.0 mmol) of triphenylphosphine were dissolved in 141 ml of THF, and the mixture was stirred at RT for 2 h. 0.70 ml (3.5 mmol) of diisopropyl azodicarboxylate and 0.62 g (2.3 mmol) of triphenylphosphine were added to the reaction mixture, and the reaction solution was stirred at RT for 1 h. The precipitated solid was filtered off and dried under high vacuum. This gave 4.6 g (52.8% of theory, purity 100%) of the title compound. The filtrate was concentrated and purified twice by silica gel chromatography (cyclohexane/ethyl acetate gradient=8/1 to 4/1). All product-containing fractions were purified again by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA). This gave another 2.16 g (25% of theory) of the target compound. (0676) LC-MS (Method 1): Rt=1.08 min (0677) MS (ESpos): m/z=375 (M+H)+ (0678) 1H-NMR (400 MHz, DMSO-d6): delta=1.34 (t, 3H), 1.79 (d, 3H), 2.25 (s, 3H), 2.58 (s, 3H), 4.33 (q, 2H), 6.17 (q, 1H), 6.73 (s, 1H), 7.06-7.16 (m, 2H), 7.37-7.48 (m, 1H), 8.67 (s, 1H).

Statistics shows that 87327-65-9 is playing an increasingly important role. we look forward to future research findings about 1-(2,6-Difluorophenyl)ethanol.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; VAKALOPOULOS, Alexandros; VALOT, Gaelle; LINDNER, Niels; FOLLMANN, Markus; WUNDER, Frank; STASCH, Johannes-Peter; MARQUARDT, Tobias; REDLICH, Gorden; DIETZ, Lisa; Ll, Volkhart Min-Jian; (94 pag.)US2017/57954; (2017); A1;,
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