Category: 887267-38-1

Electric Literature of 887267-38-1, A common heterocyclic compound, 887267-38-1, name is 3-Chloro-2,4-difluorobenzonitrile, molecular formula is C7H2ClF2N, 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.

[0184] A dry flask was charged with sodium hydride (60% suspension in mineral oil, 3.8 g, 94 mmol) and 150 ml ofdry DMF, and cooled to 0 C followed by dropwise addition of di-tert-butyl malonate via syringe. After 30 min at 0 C, asolution of 3-chloro-2,4-difluorobenzonitrile in DMF (10ml) was added over a period of 15 minutes. The ice bath wasremoved and the reaction mixture was subjected to heating at 80 C in an oil bath for 12 hrs. The mixture was cooledto RT, quenched with saturated ammonium chloride, and partitioned between water and ethyl acetate. The organic layerwas concentrated and the resulting residue purified by flash chromatography (eluted with 2->10% hexanes / ethyl acetate)to provide di-tert-butyl (2-chloro-4-cyano-3-fluorophenyl)propanedioate. 1H-NMR (400 MHz, CDCl3) delta ppm 7.68 (m, 1H),7.53 (m, 1H), 5.06 (s, 1H), 1.52 (s, 18H). LC-MS (IE, m/z): 370 [M + 1]+.

The synthetic route of 887267-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; (136 pag.)EP2755656; (2016); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 887267-38-1, name is 3-Chloro-2,4-difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Chloro-2,4-difluorobenzonitrile

t-Butyl, methyl malonate (7.5 g, 43 mmol) in DMF (50 mL) was cooled in an ice bath before NaH (60% in mineral oil, 1.0 g, 42 mmol) was added portionwise over 5 minutes with hydrogen evolution. The suspension was allowed to warm to RT for 30 minutes at which time everything was in solution. 3-Chloro-2,4-difluorobenzonit?le (5.0 g, 28.8 mmol) was added as a solid and the reaction was heated to 90 0C for 4 hours and then at RT for 12 hours. TLC (15% ethyl acetate/hexanes) indicated still some starting material but mostly product at a slightly lower Rf. The reaction was diluted with ether and quenched into water containing 2N HCl. The mixture was extracted twice with ether and the ether layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude product was taken up in 1 : 1 methanol :dichloromethane (50 mL) and 2M trimethylsilyldiazomethane in ether was added until the yellow color persisted to re-esterify any acid. The excess diazomethane was quenched with acetic acid and the mixture was reconcentrated. The product mixture was separated by flash chromatogrphy (5-10% ethyl acetate/hexanes, then 10-20%) to afford first some recovered starting material, then a mixture of product and isomeric t-butyl, methyl (R,S)-2-(2-chloro-6- cyano-3-fluorophenyl)malonate by NMR (900 mg), followed by clean title product isomer. 1H-NMR (400 MHz, CDCl3) delta ppm 1.46(s, 9H), 3.79 (s, 3H)5 5.15 (s, IH), 7.448 (d, J = 8.3 Hz, IH), 7.56 (dd, J = 6.0, 8.2, IH).

According to the analysis of related databases, 887267-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; TEUMELSAN, Nardos, H.; YANG, Lihu; ZHU, Yuping; WALSH, Shawn, P.; WO2010/129379; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts