Synthetic Route of 623-00-7,Some common heterocyclic compound, 623-00-7, name is 4-Bromobenzonitrile, molecular formula is C7H4BrN, 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.
General procedure: Preparation of biphenyl-4-carbonitrile (38): Pd(OAc)2 (2.3 mg, 1 mmol %), 4-bromo-benzonitrile (37) (182 mg, 1.0 mmol), 4,4,6-trimethyl-2-phenyl-[1,3,2] dioxaborinane (26) (224.4 mg, 1.1 mmol), Cs2CO3 (650 mg, 2 mmol), toluene (4 mL)-methanol (1 mL) were mixed together in a small reaction tube and the mixture was heated at 60 C. The reaction progress was followed by TLC (15% ethyl acetate:hexanes). After the starting materials were consumed the mixture was cooled and filtered through celite followed by washing with toluene. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (15% ethyl acetate:hexanes) to obtain the title compound in 95% yield. 1H NMR (400 MHz, CDCl3): delta 7.74-7.67 (m, 4H), 7.62-7.58 (m, 2H), 7.53-7.41 (m, 3H). 13C NMR (100.6 MHz, CDCl3): delta 145.9, 139.4, 133.7, 132.9, 132.8, 129.4, 128.9, 128.0, 127.5, 119.2, 111.1
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromobenzonitrile, its application will become more common.
Reference:
Article; Myslinska, Malgorzata; Heise, Glenn L.; Walsh, Dana J.; Tetrahedron Letters; vol. 53; 24; (2012); p. 2937 – 2941;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts