Reference of 106-39-8,Some common heterocyclic compound, 106-39-8, name is 1-Bromo-4-chlorobenzene, molecular formula is C6H4BrCl, 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: In a thermostatted bath at 25C (or 60C for compounds 18 and 28), a 25 mL Schlenk flask was charged in air with a magnetic stir bar, arylbromide (0.5 mmol), arylboronic acid (0.6 mmol), K2CO3 (0.6 mmol), 1 (26.6 mg, 1mol-%), ethanol (1.5 mL), and water (0.5 mL). The reaction mixture was kept under vigorous stirring until the GC control showed no residual aryl bromide in solution. Water (10 mL) was added to the suspension and the organics were extracted with dichloromethane (3×10 mL). The solution was dried over Na2SO4 and then passed through a column filled with silica gel (diatomaceous earths were used in the case of compound 28). Elimination of the solvent under vacuum gave the desired biaryl as white microcrystalline solid. Purity (96÷99%) was established by GC and 1H NMR. 1H and 13C{1H} NMR data of compounds 8-28. Spin multiplicity is given by s=singlet, br s=broad singlet, q=quartet, st=septet, qq=quartet of quartets, ddd=doublet of doublets of doublets, m=unresolved multiplet. 4-Chloro-4′-methyl-1,1′-biphenyl (16). Yield 96%. C13H11Cl (202.68): calcd. C 77.04, H 5.47; found C 76.95, H 5.48. 1H NMR (CDCl3): delta = 7.55-7.33 (6H, m), 7.29-7.16 (2H, m), 2.39 (3H, s, CH3) ppm. 13C NMR (CDCl3): delta = 139.5, 137.4, 137.0, 132.9, 129.5, 128.8, 128.1, 126.7, 21.0 (CH3) ppm.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-chlorobenzene, its application will become more common.
Reference:
Article; Del Zotto, Alessandro; Colussi, Sara; Trovarelli, Alessandro; Inorganica Chimica Acta; vol. 470; (2018); p. 275 – 283;,
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