Some common heterocyclic compound, 17318-08-0, name is 5-Bromo-1,3-dichloro-2-fluorobenzene, molecular formula is C6H2BrCl2F, 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. category: chlorides-buliding-blocks
To an oven dried 8 mL vial with teflon cap purged with N2 was added Zinc dust (298 mg, 4.56 mmol), DMF(1.5 mL), and iodine (57.8 mg, 0.228 mmol). To this mixture was added (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate (500 mg, 1.519 mmol), immediately followed by iodine (57.8 mg, 0.228 mmol).Pd2(dba)3 (69.6 mg, 0.076 mmol), 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl (62.4 mg, 0.152mmol), 5-bromo-1,3-dichloro-2-fluorobenzene (556 mg, 2.279 mmol) and the reaction mixture was allowedto stir at rt for 16 h. The crude mixture was diluted in 30 mL of EtOAc and DMF was removed using fouraqueous washes. The organic phase was dried over anhydrous sodium sulfate. The solution was filtered andconcentrated and the crude product was purified by silica gel chromatography using 100% hexanes to 30%EtOAc/Hexanes. The desired product was obtained as a pale yellow oil, (S)-methyl 2-((tertbutoxycarbonyl)amino)-3-(3,5-dichloro-4-fluorophenyl)propanoate, 0.102 g which was taken into next stepdirectly.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17318-08-0, its application will become more common.
Reference:
Patent; Bristol-Myers Squibb Company; Miller, Michael Matthew; Mapelli, Claudio; Allen, Martin Patrick; Bowsher, Michael S.; Boy, Kenneth M.; Gillis, Eric P.; Langley, David R.; Mull, Eric; Poirier, Maude A.; Sanghvi, Nishith; Sun, Li-Qiang; Tenney, Daniel J.; Yeung, Kap-Sun; Zhu, Juliang; Reid, Patrick C.; Scola, Paul Michael; (892 pag.)US9308236; (2016); B2;,
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