Some common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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. Recommanded Product: 1-Bromo-3,4,5-trifluorobenzene
Synthesis of diethyl 3,4,5-trifluorophenylphosphonateTrifluorobromobenzene (1.70 mL, 14.2 mmol), diethyl phosphite (2.20 mL, 17.1 mmol), 7V,7V-dicyclohexylmethylamine (4.60 mL, 21.3 mmol) and ethanol (50 mL) were all combined in a nitrogen purged round bottom flask. After stirring for 5 minutes, triphenylphosphine (223 mg, 0.85 mmol) and palladium acetate (64 mg, 0.28 mmol) were added to the flask as one. The solution was heated to 76 0C and allowed to stir overnight. The solution started as a translucent brown color but was clearer by morning. Upon cooling, a silica plug (starting with hexanes as eluent, and increasing the polarity with ethyl acetate as needed) was run and a UV-active spot (Rf = 0.35 in 1:1 hexanes: ethyl acetate) was isolated. The final product is a clear oil (3.477 g, 91 % yield). 1B NMR (400.14 MHz, CDCl3) delta 7.44 (dt, J= 14.4, 6.50 Hz 2H), 4.19 – 4.07 (m, 4H), 1.34 (t, J= 7.07 Hz, 6H). 13C(1H) NMR (100.62 MHz, CDCl3) 5 151.1 (dddd, J= 254.7, 25.4, 10.1, 2.9 Hz, 2C), 142.5 (dtd, J= 258.6, 15.1, 3.3 Hz), 125.0 (dtd, J= 194.5, 5.8, 5.2 Hz), 116.3 – 116 (m, 2C), 62.72 (d, J= 5.63 Hz, 2C), 16.16 (d, J= 6.34 Hz, 2C). 31P(1H) NMR (161.97 MHz, CDCl3): delta 14.94. Analysis calculated (found) %: C 44.79 (44.51), H 4.51 (4.65). MS (FAB, m/z): 283 (M+, 100%). Exact mass calculated (found) for [M+H]+, m/z): 283.07109 (283.07135)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 138526-69-9, its application will become more common.
Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; IMPERIAL INNOVATIONS Ltd.; HOTCHKISS, Peter; MARDER, Seth; GIORDANO, Anthony; ANTHOPOULOS, Thomas, D.; SOLVAY SA; WO2010/115854; (2010); A1;,
Bromide – Wikipedia,
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