A common compound: 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 194853-86-6
Procedure for synthesis of cyano-nilutamide (1) (Cogan, P. S.; Koch, T. H. Rational Design and Synthesis of Androgen Receptor-Targeted Nonsteroidal Anti-Androgen Ligands for the Tumor-Specific Delivery of a Doxorubicin-Formaldehyde Conjugate. J Med. Chem. 2003, 46, 5258-5270) 4-Fluoro-2-(trifluoromethyl)benzonitrile (4.02 g, 21.3 mmol) was added to Hydantoin (13.6 g, 106.3 mmol) and Potassium Carbonate (4.40 g, 31.9 mmol) in 60 mL DMF and stirred at 45C under argon for 48 hours. Reaction mixture was then diluted in ethyl acetate and washed three times with water. Organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. Column chromatography (eluent 30: 1 DCM/Methanol) gave 1 as a white solid (4.62 g, 74%). 1H NMR (400 MHz, (CD3)2-CO) delta 1.54 (6H, s), 7.80 (1H, s), 8.13 (1H, dd, J = 1.8 Hz, J = 8.4 Hz), 8.20 (1H, d, J = 8.4 Hz), 8.26 (1H, d, J = 1.8 Hz)
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 194853-86-6, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; OYELERE, Adegboyega; GRYDER, Berkley; WO2012/50868; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts