Application of 42872-73-1,Some common heterocyclic compound, 42872-73-1, name is 2-Bromo-4-methylbenzonitrile, molecular formula is C8H6BrN, 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.
A mixture of 2-bromo-4-methylbenzonitrile (2.00 g, 10.2 mmol), 5, 5, 5′, 5′- tetramethyl-2,2′-bi(l,3,2-dioxaborinane) (3.06 g, 13.6 mmol) and potassium acetate (3.00 g, 30.6 mmol) in anhydrous DMSO (10 mL), in a sealable flask, was purged with Argon for 20 min before PdChldppfj-Cl ECl? adduct (0.25 g, 0.34 mmol) was added, the flask was sealed and the reaction heated at 80 C. After 17 hrs, the reaction was cooled to RT before being partitioned between EtOAc and brine. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried (MgS04), filtered and concentrated in vacuo to afford a brown oil which solidified upon standing. Purification by Isco chromatography afforded 301 A as an off-white solid (1.96 g; 84% yield). NMR (400MHz, DMSO-d6) d 7.72 – 7.63 (m, 2H), 7.43 (dd, 7=7.9, 1.1 Hz, 1H), 3.79 (s, 4H), 2.38 (s, 3H), 0.98 (s, 6H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-methylbenzonitrile, its application will become more common.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; NARA, Susheel Jethanand; ROY, Saumya; THANGAVEL, Soodamani; CHERUKU, Srinivas; SISTLA, Ramesh Kumar; (230 pag.)WO2020/23355; (2020); A1;,
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