These common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, its 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. 60702-69-4
To a solution of (4S,5S)-4-hydroxy-5-methylpyrrolidin-2-one 7 33 (7.00 g, 60.8 mmol) in THF (120 mL) was added sodium bis(2-methoxyethoxy)aluminium dihydride (70% in toluene, 59.7 mL, 215 mmol) slowly at 5 C. After stirring at 70 C for 3 h, the reaction mixture was cooled to 5 C followed by addition of sodium carbonate decahydrate (26.1 g, 91.2 mmol). The mixture was stirred at room temperature for 16 h, diluted with THF, and the precipitate was filtered off. The filtrate was concentrated in vacuo, and the residue was dissolved in DMSO (80 mL). To the solution was added lithium carbonate (8.99 g, 122 mmol) and 2-chloro-4-fluorobenzonitrile (9.46 g, 60.9 mmol), and the mixture was stirred at 100 C for 1 h. The mixture was diluted with EtOAc and H2O, and the organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc) to give 10 (10.7 g, 74%) as a colorless solid. 1H NMR (300 MHz, CDCl3) delta: 1.18 (3H, d, J = 6.6 Hz), 1.82 (1H, d, J = 5.5 Hz), 2.01-2.14 (1H, m), 2.25-2.35 (1H, m), 3.19-3.28 (1H, m), 3.43-3.51 (1H, m), 3.89-3.98 (1H, m), 4.43-4.52 (1H, m), 6.43 (1H, dd, J = 8.9 and 2.4 Hz), 6.56 (1H, d, J = 2.4 Hz), 7.42 (1H, d, J = 8.9 Hz). MS (ESI) m/z 237 [(M+H)+].
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 60702-69-4.
Reference:
Article; Yamamoto, Satoshi; Kobayashi, Hiromi; Kaku, Tomohiro; Aikawa, Katsuji; Hara, Takahito; Yamaoka, Masuo; Kanzaki, Naoyuki; Hasuoka, Atsushi; Baba, Atsuo; Ito, Mitsuhiro; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 70 – 83;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts