Electric Literature of 17417-09-3, A common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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.
To a solution of 2-fluoro-5-nitrobenzonitrile (5.00 g, 30.1 ?unol) and 3-aminophenol (3.28 g, 30.1 itimol) in N, N- dimethylformamide (30 itiL) was added potassium carbonate (6.23 g, 45.2 itunol) , and the mixture was stirred at 600C for 2 hr. The reaction mixture was cooled to room temperature, insoluble material was filtered off and washed with ethyl acetate (150 mL) . The filtrate and washings were combined and the mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (200 mL) , washed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL) , successively, and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=20/80-»70/30) and the obtained solution was concentrated under reduced pressure. The residue was crystallized from ethyl acetate/n-hexane to give the title compound (5.09 g, 66%) as a yellow powder. 1H-NMR (DMSO-de, 300 MHz) delta 5.48 (2H, s) , 6.31 – 6.37 (IH, m) , 6.38 (IH, t, J = 2.2 Hz), 6.51 – 6.58 (IH, m) , 7.03 (IH, d, J = 9.4 Hz), 7.11 – 7.20 (IH, m) , 8.45 (IH, dd, J = 9.4, 2.8 Hz), 8.82 (IH, d, J = 2.8 Hz)
The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; OKANIWA, Masanori; TAKAGI, Terufumi; WO2010/64722; (2010); A1;,
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