General Description
FT-IR and μ-Raman spectra of 4-chloro-3-nitrobenzonitrile have been recorded in the range of 400-4000cm
-1 and 100-4000cm
-1, respectively. It has been prepred from the reaction of 4-chloro-3-nitrobenzamide and phosphorus oxychloride. Crystal structure of 4-chloro-3-nitrobenzonitrile has been reported. Molecules of 4-chloro-3-nitrobenzonitrile are linked by weak intermolecular C-H…O and C-H…N hydrogen bonds.
Synthesis
The general procedure for the synthesis of 4-chloro-3-nitrobenzonitrile from 4-chlorobenzonitrile was as follows: 4-chlorobenzonitrile (4 g, 29.2 mmol) was dissolved in 40 mL of anhydrous acetonitrile, and nitronium tetrafluoroborate (7.7 g, 58.39 mmol) was added slowly at 0 °C. The reaction mixture was stirred at room temperature for 20 hours. After completion of the reaction, the mixture was quenched by pouring it into cold water. The precipitated white solid product was collected by filtration and the filter cake was washed with cold water to remove impurities. The resulting crude product (4.0 g, 75.47% yield) could be used directly in the subsequent reaction steps without further purification.
References
[1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1252 - 1257
[2] Patent: WO2014/24056, 2014, A1. Location in patent: Page/Page column 40
[3] MedChemComm, 2017, vol. 8, # 10, p. 2003 - 2011
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 1110 - 1116
[5] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 36
