Adding a certain compound to certain chemical reactions, such as: 191478-99-6, name is Methyl 4-amino-2,6-difluorobenzoate, 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 191478-99-6, Quality Control of Methyl 4-amino-2,6-difluorobenzoate
Phenylmethanethiol (80.0 g, 645 mmol) was dissolved in anhydrous tetrahydrofuran (600 ml), and 60% sodium hydride (45.0 g, 1.13 mol) was added thereto, followed by stirring at room temperature for 30 minutes. To this reaction solution, 5-bromo-2-chloropyridine (123 g, 640 mmol) was added, followed by stirring at room temperature for 3 hours. The reaction solution was diluted with water, followed by extraction with diethyl ether. The extraction liquids were combined, washed with a saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. Then, the solvent was removed. A compound (250 g, 0.90 mol) obtained by repeating the-above described process was suspended in a mixture solvent of acetic acid (2250 ml) and water (750 ml), and N-chlorosuccinimide (340 g, 2.60 mol) was added thereto, followed by stirring at room temperature for 2 hours. The reaction solution was diluted with water, followed by extraction with methylene chloride. The extraction liquids were combined, washed with a saturated aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous sodium sulfate. Then, the solvent was removed. The obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=30:1). The obtained compound (47.0 g, 185 mmol) and methyl 4-amino-2,6-difluorobenzoate (26.0 g, 139 mmol) were suspended in methylene chloride (1000 ml), and pyridine (30 ml) was added thereto, followed by stirring at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=4:1) to obtain the title compound (50 g, 15% over three steps). [0183] 1H NMR (d-DMSO, 400 MHz): delta 8.92 (d, J=1.6 Hz, 1H), 8.41-8.38 (m, 1H), 8.07 (d, J=8.4 Hz, 1H), 6.93 (d, J=10 Hz, 2H), 3.81 (s, 3H).; MS (ESI) m/z 407 (M+H)+
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Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
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