Some common heterocyclic compound, 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF4, 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. Application In Synthesis of 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene
Reference Example 54 1-[2-fluoro-4-(trifluoromethyl)phenyl]pyrrolidin-3-ol; A solution of 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (4.6 g), 3-hydroxypyrrolidine (1.5 g), palladium(II) acetate (137 mg), (+/-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.07 g) and cesium carbonate (16.8 g) in toluene (90 mL) was stirred under an argon gas atmosphere at 85C for 16 hr. After cooling to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10 – 65:35) to give the title compound (2.82 g, yield 66%) as a gray solid. 1H-NMR (300 MHz, CDCl3) delta:1.63 (d, J = 4.5 Hz, 1 H), 1.96 – 2.22 (m, 2 H), 3.40 – 3.57 (m, 2 H), 3.61 – 3.81 (m, 2 H), 4.51 – 4.66 (m, 1 H), 6.64 (t, J = 9.1 Hz, 1 H), 7.15 – 7.25 (m, 2 H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40161-54-4, its application will become more common.
Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2295406; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary