Some common heterocyclic compound, 64321-95-5, name is Methyl 2-amino-3-(trifluoromethyl)benzoate, molecular formula is C9H8F3NO2, 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. Quality Control of Methyl 2-amino-3-(trifluoromethyl)benzoate
To a stirred solution of No.105 methyl 2-amino-3-(trifluoromethyl)benzoate (IV-34, 3.6 g, 16.4 mmol) in No.107 CH3CN (22 mL) was added No.108 HBr (48% (aq), 20.3 mL) dropwise at 0C. over 10 min. Then, No.71 NaNO2 (1.25 g, 18.1 mmol) in No.21 water (5 mL) was added dropwise over 1 h at 0C. with vigorous stirring. After addition, the solution was stirred for 5 min at 0C. followed by the addition of No.109 CuBr (2.71 g, 18.9 mmol) in portions over 30 min. The mixture was heated at 70C. for 1 h then cooled again to 0C. before being diluted with water (40 mL) and extraction with EtOAc (350 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (Na2SO4), concentrated to dryness under reduced pressure, and chromatographed (ethyl acetate/hexanes, 1:9) to afford a clear No.96 oil (3.47 g, 75%). 1H NMR (500 MHz, CDCl3) delta 7.74 (dd, J=8.0, 1.7 Hz, 1H), 7.69 (dd, J=7.7, 1.7 Hz, 1H), 7.43 (t, J=7.8 Hz, 1H), 3.92 (s, 3H). 13C NMR (126 MHz, CDCl3) delta 166.77, 136.82, 133.04, 131.53 (q, J=31.0 Hz), 129.78 (q, J=5.6 Hz), 127.38, 122.77 (q, J=273.8 Hz), 118.56, 52.93. 19F NMR (376 MHz, CDCl3) delta -62.78 (s, 3F). HRMS [M+H]+ Calcd for C9H6BrF3O2 282.9576; found 282.9575.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64321-95-5, its application will become more common.
Reference:
Patent; Northwestern University; Silverman, Richard B.; Le, Hoang V.; McLeod, Rima L.; Hawker, Dustin D.; (53 pag.)US2018/98952; (2018); A1;,
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