These common heterocyclic compound, 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, 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. SDS of cas: 1009-35-4
To a flask charged with 4-fluoro-3-nitrobenzonitrile (0.984 g, 5.92 mmol) in ACN (19.75 mL), was added trans-n-boc- 1 ,4-cyclohexanediamine (1.269 g, 5.92 mmol) and TEA (1.651 mL, 1 1.85 mmol). The resulting mixture was stirred at 80¡ãC for 3 h leading to complete conversion. The mixture was cooled to RT. The resulting solid was filtered, washed with water and dried to give tert-butyl ((lr,4r)-4-((4- cyano-2-nitrophenyl) amino)cyclohexyl)carbamate (1.93 g, 5.36 mmol, 90 percent yield) as yellow solid, which was used for next step without further purification. lH NMR (400 MHz, DMSO-i/6) delta ppm 8.29 – 8.37 (m, 1 H) 7.96 – 8.10 (m, 1 H) 7.53 – 7.71 (m, 1 H) 7.13 (d, J=9.29 Hz, 1 H) 6.64 (d, J=7.82 Hz, 1 H) 3.34 – 3.62 (m, 1 H) 3.09 (d, J=2.25 Hz, 1 H) 1.81 (d, J=10.27 Hz, 2 H) 1.65 (d, J=10.47 Hz, 2 H) 1.09 – 1.38 (m, 13 H). m/z (ESI) 361.2
The synthetic route of 4-Fluoro-3-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.
Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John L.; CHAKKA, Nagasree; DIMAURO, Erin F.; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Xin; WO2014/36022; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts