Reference of 349-55-3, The chemical industry reduces the impact on the environment during synthesis 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline, I believe this compound will play a more active role in future production and life.
3-methoxy-5- (trifluoromethyl)aniline (100 mg, 0.52 mmol) was dissolved in CHC13 (5.2 mL) and t-butyl nitrite (124 muL, 1.05 mmol) was added dropwise by syringe. Iodine (266 mg, 1.05 mmol) was added and then the reaction was slowly heated to 50C and was maintained at this temperature for an hour and thirty minutes. The reaction was then cooled to room temperature and poured into aq. NaHS03 (50 mL). The mixture was extracted with EtOAc (50 mL) and the organic extracts were washed with aq. NaHS03 (3 X 50 mL) and brine (20 mL), dried over Na2S04, filtered, and concentrated. Purification by flash chromatography with 1% to 15% EtOAc/hexanes afforded 1-iodo-3-methoxy-5-(trifluoromethyl)benzene. Rf= 0.75 (25% EtOAc/hexanes). ‘H NMR (CDC13, 500 MHz) 8 7.53 (s, 1H), 7.41 (s, 1H), 7.09 (s, 1H), 3.82 (s, 3H). Step B: 3-Methoxy-5-(trifluoromethyl)benzonitrile To a solution of 1-iodo-3-methoxy-5-(trifluoromethyl)benzene (200 mg, 0.66 mmol) in DMF (2 mL) was added CuCN (300 mg, 5.0 mmol). The reaction was stirred at 100C for 24 hours and then poured into aq. NH3 (40 mL). The mixture was extracted with EtOAc (70 mL) and the organic extracts were washed with brine (25 mL), dried over Na2S04, filtered, and concentrated. Purification by flash chromatography with 5% to 80% EtOAc/hexanes afforded 3-methoxy-5- (trifluoromethyl)benzonitrile. 0.64 (50% EtOAc/hexanes). ‘H NMR (CDC13, 600 MHz) 8 7.47 (s, 1H), 7.34 (s, 1H), 7.31 (s, 1H), 3.89 (s, 3H). Step C: 3-Methoxy-5-(trifluoromethyl)benzaldehyde A mixture of 3-methoxy-5- (trifluoromethyl)benzonitrile mg, 0.43 mmol) and Pt02 (9.8 mg, 0.043 mmol) in 88% formic acid (651 muL) was heated to 60C. The reaction was stirred at this temperature for thirty minutes. The reaction was then cooled to room temperature, diluted with hexanes (5 mL), loaded on a silica gel column, and purified with 1% to 15% EtOAc/hexanes to afford 3-methoxy-5- (trifluoromethyl) benzaldehyde. Rf= 0.56 (25% EtOAc/hexanes). ‘H NMR (CDCl3,500 MHz) 8 10.01 (s, 1H), 7.71 (s, 1H), 7.56 (s, 1H), 7.39 (s, 1H), 3.92 (s, 3H).
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