Application of 179897-90-6,Some common heterocyclic compound, 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, molecular formula is C6H2Br2ClF, 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.
To a round bottom flask under nitrogen fitted with a stir bar was added 1- chloro-2,6-dibromo-4-fluorobenzene (14.36 g, 49.8 mmol), pivalamide (5.04 g, 49.8 mmol), cesium carbonate (21.09 g, 64.7 mmol) and dioxane (250 mL). The reaction mixture was sparged with nitrogen and Pd(dba)2 (1.43 g, 2.490 mmol) and 5-bis(diphenylphosphino)-9,9- dimethylxanthene (XANTPHOS, 2.02 g, 3.49 mmol) were added. The reaction was then sealed and heated in an oil bath at 70 C for 18 h. The reaction was allowed to cool to r.t and was partitioned between a saturated aqueous solution of NH4C1 and EtOAc. The layers were separated and the aqueous portion was extracted with EtOAc (2 X). The combined organic portions were washed with water, brine, dried (Na2S04), filtered, concentrated, and adsorbed onto silica gel. Purification by flash chromatography on silica gel using an EtO Ac- heptane (1-20%) elution gradient afforded N- (3-bromo-2-chloro-5-fluorphenyl)pivalamide (1 1.0 g, 33.8 mmol, 68 %) as a white crystalline solid. LCMS (m/z): 309.9 (MH+), tR = 1.1 1
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-2-chloro-5-fluorobenzene, its application will become more common.
Reference:
Patent; NOVARTIS AG; MADERA, Ann Marie; POON, Daniel; SMITH, Aaron; WO2011/161216; (2011); A1;,
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