654-01-3, Name is 2-(2,6-Difluorophenyl)acetonitrile, 654-01-3, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.
A mixture of 15.3 g (100 mmol) of 2-(2,6difluorophenyl)acetonitrile, 152.5 g (70 mL, 812 mmol) of dibromoethane, and 32.7 g (144 mmol) of Et3BnN+Cl- was isolated from moisture and carbon dioxide and vigorously stirred at 60. A solution prepared from 95 g (1430 mmol, ?84.5%) of KOH and 95 mL of water was then added dropwise; the mixture was stirred during 6 h at 60-65C, and left overnight. On the next day, the reaction mixture was extracted with t-BuOMe (3¡Á100 mL), the combined organic fractions were evaporated, and residual water was removed via azeotropic distillation with toluene. Then 60 mL of water and 40 mL of concentrated sulfuric acid were added to the obtained 1-(2,6-difluorophenyl)cyclopropanecarbonitrile, and the mixture was refluxed during 4 h. The reaction mass was cooled to ambient; the precipitate was filtered off and dried. Yield 17.82 g (90%), mp 156-157 (toluene). IR spectrum, nu, cm-1: 412 s, 772 m, 946 m, 994 m, 1048 s, 1246 m, 1270 m, 1306 m, 1324 m, 1414 m, 1468 m, 1474 m, 1504 s, 1624 m, 1666 m, 1726 s. 1 NMR spectrum (400.16 MHz, DMSO-d6), delta, ppm: 1.18 m (2H, 2eq, c-Pr), 1.58 m (2H, 2ax, c-Pr), 7.03 m (2H, 3,5H), 7.36 m (1H, C4H), 12.54 br.s (1H, OH). Mass spectrum (EI), m/z (Irel, %): 197.9 (100) [M]+, 153.0 (37) [M – COOH)]+, 133.0 (35) [M – COOH – HF]+, 127.2 (32) [2,6-F2C6H3CH2]+. Found, %: C 60.50; H 4.08. C10H8F2O2. Calculated, %: C 60.61; H 4.07.
Statistics shows that 2-(2,6-Difluorophenyl)acetonitrile is playing an increasingly important role. we look forward to future research findings about 654-01-3.
Reference:
Article; Novakov; Yablokov; Navrotskii; Mkrtchyan; Vernigora; Babushkin; Kachala; Ruchko; Russian Journal of General Chemistry; vol. 87; 2; (2017); p. 224 – 230; Zh. Obshch. Khim.; vol. 87; 2; (2017); p. 247 – 254,8;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts