These common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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. Recommanded Product: 4-Cyano-3-trifluoromethylaniline
To a solution of 4-amino-2- (trifluoromethyl) benzonitrile(XVII-I) (1.6 eq.) in THF (8.5 mL x mmol), cooled at -100C,LHMDS (4.5 eq.) was added drop wise. The reaction mixture was than stirred at this temperature for 40 min and HMPA(10% of the total THF) was added to the solution. After 5 min stirring, a solution of the ester XVIII-I (1 eq.) in THF (7 mL x mmol) was added to the reaction mixture. After 30 min at -100C, the solution was stirred 12h at room temperature. The reaction mixture was than quenched with 0. IN HCl and extracted with EtOAc. The crude material was purified by silica gel column chromatography. Yields range from 60 to 80%.(.R) -XXIV-3: 1H NMR (400 MHz, CDCl3) : 8.53 (broad s, IH) 7.63-7.72 (m, 2H), 7.50-7.55 (m, IH), 7.34-7.40 (m, 2H), 7.15-7.19 (m, 5H), 6.87 (dd, J= 8.8 Hz, IH) 3.87 (d, J= 14.4 Hz, IH), 3.45 (s, IH) . 3.22 (d, J= 13.6Hz, IH), 3.11 (d, J= 13.6Hz, IH), 2.95 (d, J= 14.4Hz, IH, CH2) . 13C NMR (100 MHz, CDCl3) Relevant: 172.1, 161.8 (d, J= 248Hz) 141.0,135.8, 134.5, 134.2 (d, J= 8.5Hz), 130.5, 128.8, 127.7, 122.6 (q) , 122.0, 117.6 (q, J= 5Hz) , 116.5 (d, J= 22.1Hz) 115.6, 105.0.
The synthetic route of 4-Cyano-3-trifluoromethylaniline has been constantly updated, and we look forward to future research findings.
Reference:
Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; ISTITUTO SCIENTIFICO ROMAGNOLO PER LO STUDIO E LA CURA DEI TUMORI (I.R.S.T.) S.R.L.; VARCHI, Greta; TESEI, Anna; GUERRINI, Andrea; BRIGLIADORI, Giovanni; WO2010/116342; (2010); A2;,
Nitrile – Wikipedia,
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