Category: 13519-90-9

Synthetic Route of 13519-90-9, These common heterocyclic compound, 13519-90-9, name is 4-Fluoroisophthalonitrile, 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.

4-hydroxytetrahydropyran (14 g, 140 mmol) was taken up in tetrahydrofuran (300 mL) and cooled in an ice-water bath. Potassium tert-butoxide (17 g, 150 mmol) was added, and the reaction mixture was stirred for 20 minutes in the bath before the addition of 4-fluoroisophthalonitrile (10 g, 68 mmol). The mixture continued to stir in the bath for 5 minutes before the removal of the bath. The mixture was stirred at room temperature overnight and then concentrated almost to dryness under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous phase was extracted three times with ethyl acetate. The combined organics were washed once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, concentrated to dryness under reduced pressure. The residue was recrystallized from methanol to provide 4-((tetrahydro-2H-pyran-4-yl)oxy)isophthalonitrile. 1H NMR (400 MHz, DMSO-d6) delta 8.42 (d, J=2.1 Hz, 1H), 8.16 (dd, J=8.9, 2.1 Hz, 1H), 7.60 (d, J=9.0 Hz, 1H), 5.01 (m, 1H), 3.88 (m, 2H), 3.57 (m, 2H), 2.05 (m, 2H), 1.70 (m, 2H).

The synthetic route of 13519-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Sciences, Inc.; Du, Zhimin; Guerrero, Juan A.; Kaplan, Joshua A.; Knox, JR., John E.; Lo, Jennifer R.; Mitchell, Scott A.; Naduthambi, Devan; Phillips, Barton W.; Venkataramani, Chandrasekar; Wang, Peiyuan; Watkins, William J.; Zhao, Zhongdong; (593 pag.)US2016/96827; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 13519-90-9, A common heterocyclic compound, 13519-90-9, name is 4-Fluoroisophthalonitrile, molecular formula is C8H3FN2, 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.

To (1R,3S)-cyclohexane-1,3-diamine (1.0 g, 8.8 mmol) and 4-fluoroisophthalonitrile (2.7 g, 18.4 mmol)Triethylamine (5.4 ml) was added to a solution of 30 ml of dimethyl sulfoxide. The mixture was purged with nitrogen and heated to stir at 150 C for 3 hours. After cooling to room temperature, the reaction mixture was diluted with water (100 ml) and extracted three times with dichloromethane (100 ml). The organic extracts were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography(230-600 mesh silica gel) purified,Elute with 0-80% ethyl acetate / hexane,Get the title compound,It was a white solid (2.6 g, 81% yield).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Sichuan Yi Lite Bio-pharmaceutical Co., Ltd.; Jiao Guansheng; Zhang Chengpan; (13 pag.)CN109160888; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts