Application of 58534-95-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 58534-95-5 name is 3-Bromo-2-fluoroaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
General procedure: A 100 mL round bottom flask equipped with a stirbar and condenser was charged with 3-bromo-2-methylaniline (2.74 ml, 22.25 mmol), sodium 3-nitrobenzenesulfonate (8.93 g, 39.7 mmol), and 2-methylpropane-1,2,3-triol (6.61 g, 62.3 mmol). The mixture was then taken up in water (3.85 mL) and then carefully treated with concentrated sulfuric acid (7.12 mL). The reaction mixture was then heated to 150 C with stirring. After reaching 140 C the reaction was stopped and all glassware was washed alternatingly with 1 N aq sodium hydroxide and dichloromethane to 250 mL total volume into a 400 mL beaker equipped with a stirbar. The aqueous layer was adjusted to pH 8 with SN aq sodium hydroxide and the mixture stirred for ~1 h. The mixture wastransferred to a 1 L separatory funnel, diluted with ~400 mL dichloromethane, and the layers were separated. The resulting emulsion was treated with ~200 mL saturated brine and allowed to sit overnight to separate the layers. The organic layer was isolated and the aqueous re-extracted with an additional quantity of dichloromethane. The organics were then pooled, dried over sodium sulfate, filtered, and concentrated to a residue. Theresidue was purified by flash chromatography (15-65% dichloromethane:hexanes). Fractions containing the desired material were pooled and concentrated to a residue. The residue was then taken up in dichloromethane and extracted repeatedly with 1 N aq hydrochloric acid. The organic layer was isolated and the aqueous re-extracted with an additional portion of dichloromethane. The organics were then pooled, dried oversodium sulfate, filtered, and concentrated to afford the title compound as a light orange solid (0.995 g, 4.00 mmol, 18% yield). Following the procedure described in Example 15a using 3-bromo-2-fluoroanilineand propane-1,2,3-triol afforded the title compound as a solid (75%). 1H NMR (400 MHz,dichloromethane-d2) ppm 7.44 – 7.53 (m, 2H) 7.61 (dd, J=8.84, 6.06 Hz, 1H) 8.15 (dt,J=8.34, 1 .52 Hz, 1H) 8.92 (dd, J=4.29, 1.52 Hz, 1H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-2-fluoroaniline, and friends who are interested can also refer to it.
Reference:
Patent; GLAXOSMITHKLINE LLC; MOORE, Michael, Lee; PARRISH, Cynthia, Ann; SQUIRE, Michael, Damien; WO2013/52716; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary