Application of 17417-09-3, A common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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 a solution of 2(H)-1,2,3-triazole (0.913 g, 13.24 mmol) in DMF (15 mL) was added portionwise sodium hydride (60% suspension in mineral oil, 0.530 g, 13.24 mmol) at rt and then stirred the mixture for 1H at room temperature. The reaction mixture was then cooled back down to OeC, and a solution of 2-fluoro-5-nitrobenzonitrile (2.0 g, 12.04 mmol) in DMF (10 mL) was added dropwise. The resulting mixture was stirred for 1.5 h at OeC and then at RT for 1.5 h. The mixture was quenched with ice cooled water and extracted with EtOAc (2/150 mL). The combined organic layers were washed with water (2/1,50 mL), brine (50 mL), dried (Na2SC>4) and filtered. The filtrate was rotary evaporated to leave a crude which was purified by flash column chromatography (silica gel, 20-30% EtOAc in hexanes as eluent) to give 5-nitro-2-(2H-1,2,3-triazol-2-yl)benzonitrile (1.2 g, 46.3% yield) & 5-nitro-2-(1H-1,2,3-triazol-1-yl)benzonitrile (0.7 g, 27.0% yield). 5-nitro-2-(2H-1,2,3-triazol-2-yl)benzonitrile: 1HNMR (400 MHz, DMSO-d6) ||8.93 (d, J = 2.5 Hz, 1H), 8.68 (dd, J = 8.5, 2.5 Hz, 1H), 8.44 (s, 2H), 8.40 (d, J = 8.5 Hz, 1H). ESI-MS (m/z) 216.04 (MH)+. 5-nitro-2-(1H-1,2,3-triazol-1-yl)benzonitrile: 1HNMR (400 MHz, DMSO-d6) ||9.05 (d, J = 2.5 Hz, 1H), 8.95 (d, J = 1.3 Hz, 1H), 8.75 (dd, J = 8.5, 2.5 Hz, 1H), 8.20 (d,J = 8.5 Hz, 1H), 8.15 (d, J = 1.3 Hz, 1H); ESI-MS (m/ z) 216.00 (MH)+.
The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.