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. 63069-50-1 name is 4-Amino-3-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. 63069-50-1
Specifically, oxalyl chloride (0.71 mL, 8.24 mmol) was added over 10 min to a solution of oleic acid (2 mL, 6.34 mmol) and DMF (3 drops) in DCM (10 mL) at 0 C, and the solution stirred at room temperature overnight. The solvent and excess oxalyl chloride was removed in vacuo and the residue redissolved in DCM (10 mL). This solution was added dropwise to a solution of 3-fluoro-4-aminobenzonitrile (0.70 g, 5.14 mmol) in DCM (10 mL) and ET.3N (1 mL) that had been cooled in an ice bath. Upon complete addition, the solution was stirred at room temperature overnight. The solution was washed with saturated Na2C03 solution (3 chi 20 mL), H2O (20 mL), and brine (20 mL), and dried over MgS04. The resulting residue was subjected to column chromatography, using a gradient elution of EtOAc/petroleum spirits to afford the product as a white. (0541) [00403] Yield: 1 .59 a (61 %). [00404] FT-I (ATR) V^/crrr1 : 3319 br w. 2919 m. 2850 m. 2236 w. 1681 s. 1616 w. 1589 m, 1519 s. 1 H-NMR delta/ppm (d6-DMSO): 10.07 (1 H, s, NH), 8.33 (1 H, dd, 3JH,H = 8.5 Hz, 4 H,F = 7.9 Hz, Ar CH), 7.89 (1 H, dd, 3JH,F = 1 1 .0 Hz, 4 H,H = 2.0 Hz, Ar CH), 7.66 (1 H, ddd, 3JH,H = 8.5 Hz, 4JH,H = 2.0 Hz, 5JH,F = 0.9 Hz, Ar CH), 5.29 – 5.40 (2 chi 1 H, 2 chi m, 2 chi olefinic CH), 2.47 (2H, m, NHCOCH2) , 1 .96 – 2.04 (2 x 2H, 2 x m, 2 x CH2), 1 .61 (2H, m, CH2), 1 .23 – 1 .37 (10 chi 2H, 10 chi m, 10 chi CH2), 0.87 (3H, m, CH3). 13C-NMR delta/ppm (d6-DMSO): 172.4 (CONH), 151 .6 (d, 1 JC,F = 247 Hz, Ar CF), 131 .7 (d, 2JC,F = 1 1 .1 Hz, Ar C), 129.6 (olefinic CH), 129.5 (olefinic CH), 129.3 (d, 3JC,F = 3.4 Hz, Ar CH), 122.9 (d, 4JC,F = 2.7 Hz, Ar CH), 1 19.2 (d, 2JC,F = 23.3 Hz, Ar CH), 1 17.9 (d, 4JC,F = 2.7 Hz, CN), 105.7 (d, 3JC,F = 9.4 Hz, Ar C), 35.9 (NHCOCH2), 31 .3 (CH2) , 29.09 (CH2), 29.08 (CH2), 28.8 (CH2), 28.7 (CH2), 28.62 (CH2), 28.59 (CH2), 28.55 (CH2), 28.5 (CH2), 26.6 (CH2), 24.9 (CH2), 22.1 (CH2), 13.9 (CH3).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-fluorobenzonitrile, and friends who are interested can also refer to it.
Reference:
Patent; CURTIN UNIVERSITY; FALASCA, Marco; MASSI, Massimiliano; SIMPSON, Peter, Vernon; (181 pag.)WO2019/40992; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts