Some common heterocyclic compound, 185147-07-3, name is 2-Fluoro-3-methylbenzonitrile, molecular formula is C8H6FN, 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. name: 2-Fluoro-3-methylbenzonitrile
Intermediate 20: 3-Methyl-2-(2H-1 ,2,3-triazol-2-yl)benzonitrile.To a mixture of 2-fluoro-3-methylbenzonitrile (4.0 g, 29.6 mmol) and 2H-1 ,2,3- triazole (2.04 g, 29.6 mmol) in DMF (80 mL) was added potassium carbonate (8.26 g, 59.2 mmol). The resulting mixture was heated to 120 C for 2h. The mixture was cooled, diluted with water and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (S1O2, ethyl acetate/hexanes, gradient 0-50%) to yield the title compound (1 .5 g, 26%). MS (ESI) mass calcd. for Ci0H8N4,184.2; m/z found, 185.1 [M+H]+. 1 H NMR (500 MHz, CDCI3): 7.95 (s, 2H), 7.66 (d, J = 7.7, 0.7 Hz, 1 H), 7.59 (d, J = 7.8, 0.6 Hz, 1 H), 7.50 (dd, J = 9.8, 5.7 Hz, 1 H), 2.20 (s, 3H).Intermediate 21 : 3-Methyl-2-(1 H-1 ,2,3-triazol-1 -yl)benzonitrile.The title compound was also a product of the synthesis of Intermediate 20 (3.1 g, 56%). MS (ESI) mass calcd. for CioH8N4, 184.2; m/z found, 185.1 [M+H]+. 1 H NMR (500 MHz, CDCI3) : 7.94 (d, J = 2.1 Hz, 1 H), 7.87 (d, J = 1 .1 Hz, 1 H), 7.71 – 7.67 (m, 1 H), 7.67 – 7.62 (m, 1 H), 7.56 (dd, J = 9.7, 5.8 Hz, 1 H), 2.17 (s 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 185147-07-3, its application will become more common.
Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
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