These common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, 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. 33863-76-2
EXAMPLE 13-Chloro-5-{[5-chloro-l-(lH-pyrazolo[3,4-]pyridin-3-ylmethyl)-lH-indazol-4- yl] oxy } benzonitrileStep 1 : 3-Bromo-5-chlorophenyl 2-chloro-5-fluorophenyl ether; To a solution of 2-chloro-5-fluorophenol ( 82.3 g, 562 mmol) and l-bromo-3- chloro-5-fluorobenzene (124g, 590 mmol) in NMP (200 mL) was added potassium carbonate (155g, 1.123mol). The resulting mixture was then heated to 1400C and maintained at 14O0C for 30 hours, after which the mixture was poured into water (1500 mL) and extracted with EtOAc (2500 + 1500 mL). The combined extracts were washed with water and brine. This solution was concentrated on the rotary evaporator and the residue was distilled at high vacuum at 135-1900C to give the title compound as a clear, colorless liquid. leta NMR (CDCI3) delta 7.45 (dd, 1eta, J=9.0 and 4.5 hz), 7.28(dd, 1eta, J=I .7Hz), 7.26(s, IH), 7.00(dd, Ih, J=I .95Hz), 6.92(ddd, IH, J=10.5, 7.6 and 2.7Hz), 6.89(dd, IH, J=I.95Hz).
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 33863-76-2.
Reference:
Patent; MERCK & CO., INC.; WO2008/76223; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics