These common heterocyclic compound, 139152-08-2, name is 4,5-Dichlorophthalonitrile, 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. Quality Control of 4,5-Dichlorophthalonitrile
Compound 2 (1.5 g, 6.1 mmol) was dissolved in 40 mL anhydrous DMF. Anhydrous CsF (1.9 g, 12.2 mmol) was then added to the solution and the mixture was allowed to stir for 10 min at room temperature. A solution of 4,5-dichlorophthalonitrile (1.0 g, 5.1 mmol) in 10 mL anhydrous DMF was then added and the reaction mixture was stirred for 24 hrs at room temperature. After completion, the salt was filtered out using Buchner funnel and the crude mixture was diluted in 100 mL water and extracted with DCM (2¡Á50 mL). DCM was then concentrated under reduced pressure and the crude material was purified by column chromatography using (2:8) EtOAc/hexane solvent system as an eluent to obtain the desired product 5 as a white solid in 1.7 g (85% yield); mp is 106.2 C. Elemental analysis calculated (%) for C23H17ClN2O3: C, 68.23; H, 4.23; N, 6.92. Found: C, 68.03; H, 4.22; N, 6.78; FT-IR, numax/cm-1 3297.68, 2883.06, 2611.14, 2232.20; 1H-NMR (600 MHz, DMSO-d6, 25 0C): delta=2.38 (s, 3H), 3.33 (t, J=2.3 Hz, 2H), 4.02 (t, J=2.3 Hz, 4H), 4.32 (dd, J=10.9, 35.0 Hz, 4H), 7.09 (s, 1H), 7.35 (s, 2H), 8.47 (s, 1H); 13C-NMR (150 MHz, DMSO-d6, 25 0C): delta=20.5, 57.7, 77.2, 79.5, 108.5, 114.8, 114.9, 115.0, 119.9, 126.8, 130.0, 131.4, 135.6, 136.4, 146.6, 157.6; HRMS [M]+ calcd for C23H7ClN2O3: 404.0928, found: 404.0922.
The synthetic route of 4,5-Dichlorophthalonitrile has been constantly updated, and we look forward to future research findings.
Reference:
Patent; KUWAIT UNIVERSITY; MAKHSEED, SAAD A.; HUSAIN, ALI A.; GANESAN, ASAITHAMPI; DURMUS, MAHMUT; US2020/102267; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts