Application of 859855-53-1, 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. 859855-53-1 name is 3-Amino-4-fluorobenzonitrile, 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.
A solution of NaNO2 (380 mg, 5.51 mmol) in water (2 mL) was added to a suspension of 3-amino-4-fluorobenzonitrile (500 mg, 3.67 mmol) in concentrated HCl (5 mL) at 0 C over 5 mins., and the solution stirred for a further 30 mins. Meanwhile, AcOH (5 mL) was saturated with SO2, then CuCl2.2H2O (188 mg, 1.10 mmol) was added and SO2 bubbled through for a further 5 mins. The AcOH mixture was cooled to 5 C, then the diazonium solution added over 5 mins. The resulting mixture was stirred for a further 1h at 0 C then 1h at room temperature. The solution was diluted with water and extracted twice with CH2Cl2. The combined organic extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo. Chromatography (hexanes: EtOAc 19:1 to 9:1) gave the title compound as a yellow oil (569 mg, 71%). 1H NMR delta (400 MHz, CDCl3) 8.31 (dd, J 6.2, 2.1 Hz, 1H), 8.04 (ddd, J 8.7, 4.3, 2.1 Hz, 1H), 7.51 (t, J 8.7 Hz, 1H). LCMS (APCI-) 200 (M-Cl+O, 100%).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Amino-4-fluorobenzonitrile, and friends who are interested can also refer to it.
Reference:
Article; Kendall, Jackie D.; Giddens, Anna C.; Tsang, Kit Yee; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Jamieson, Stephen M.F.; Rewcastle, Gordon W.; Baguley, Bruce C.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 2; (2017); p. 187 – 190;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts