Application of 873-38-1,Some common heterocyclic compound, 873-38-1, name is 2-Bromo-4-chloroaniline, molecular formula is C6H5BrClN, 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.
In a 20 mL microwave vial was added 2-bromo-4-chloroaniline (3 g, 14.53mmol), 4,4,5,5 -tetramethyl-2-(tetramethyl-1 ,3,2-dioxaborolan-2-yl)- 1 ,3,2-dioxaborolane(5.53 g, 21.80 mmol), KOAc (3.66 g, 37.3 mmol), Pd(dppf)C12-CH2C12 adduct (0.32 g, 0.44 mmol) and DMSO (9 mL). The resulting suspension was purged with N2, capped and heated at 80 C for 22 h. The reaction was cooled to rt. Water was added to dissolve the salts, then the reaction was filtered. The remaining solid was suspended in DCM andthe insoluble solid was filtered. The filtrate was concentrated and then purified by normalphase chromatography to give 4-chloro-2-(tetramethyl- 1 ,3,2-dioxaborolan- 2-yl)aniline(3.15 g, 86 % yield) as a white solid. MS (ESI) m/z: 172.3 (M-C6H1o+H). ?H NMR(400MHz, CDC13) 7.54 (d, J=2.6 Hz, 1H), 7.13 (dd, J=8.8, 2.6 Hz, 1H), 6.52 (d, J=8.6Hz, 1H), 4.72 (br. s., 2H), 1.34 (s, 12H).
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-chloroaniline, its application will become more common.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PABBISETTY, Kumar Balashanmuga; CORTE, James R.; DILGER, Andrew K.; EWING, William R.; ZHU, Yeheng; (178 pag.)WO2017/19819; (2017); A1;,
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