Electric Literature of 115843-99-7,Some common heterocyclic compound, 115843-99-7, name is 4-Bromo-3-chloro-2-fluoroaniline, molecular formula is C6H4BrClFN, 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.
Example 9: Synthesis of boronate fragment 9b (used in Example 43)Anhydrous DMF (60 mL) is added to a flask charged with bromide 9a (5.00 g, 22.2 mmol), /?/s-(pinacolato)diborone (8.48 g, 33.4 mmol) and potassium acetate (6.35 g, 66.8 mmol) and the resulting suspension is deoxygenated by bubbling a stream of N2 gas through the mixture for 45 min. 1 ,1′-bis(diphenylphosphino)ferrocene (2.73 g, 3.34 mmol) is then added and the mixture is deoxygenated for approximately a further 5 min and is then heated to 950C. After 16 h, the dark reaction mixture is cooled, extracted with EtOAc (500 mL and 300 mL) and washed with 1 :1 water/brine (600 mL) and brine (600 mL). The combined extracts are dried over anhydrous MgSO4, filtered and evaporated to a black syrup which is purified by flash column chromatography (EtOAc/hexanes) to afford the boronate 9b as white solid contaminated with <25 % of the diboron reagent (4.24 g, 62% yield).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-chloro-2-fluoroaniline, its application will become more common.
Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/62285; (2009); A1;,
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