In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 367-22-6, name is 4-Chloro-3-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Chloro-3-fluoroaniline
A mixture of 5-amino-3-methyl-1 ,2-thiazole-4-carboxylic acid [CAS-RN: 22131 -51-7, for the synthesis, please see: J. Goerdeler, H. Horn, Chem. Ber. (1963),96, 1551-1560.] (5.00 g, 9.93 mmol, 1.0 eq) and thionyl chloride (20.7 mL,284 mmol, 9.0 eq) was stirred at 80 C for 2 h. After cooling, the volatilecomponents were removed in vacuo. The crude acid chloride was diluted with toluene and concentrated at the rotary evaporator. This process was repeated one more time. The acid chloride (1.75 g, 9.93 mmol, 1.0 eq) observed this way was dissolved in THF (15 mL). Then, 4-chloro-3-fluoroaniline [CAS-RN: 367-22-6] (2.89 mL, 19.9 mmol, 2.0 eq) and triethyl amine (2.01 mL, 19.9 mmol, 2.0 eq)was added. The reaction mixture was stirred at rt overnight. After addition of water the crude reaction mixture was acidified with 1M hydrochloric acid and extracted with EtOAc. The organic phase was washed with brine and dried with sodium sulfate. After removal of the volatile components the product was crystallized from dichloromethane and methanol. The precipitate was isolated by filtration and dried under high vacuum to give the title compound (600 mg,-21% yield of theory based on the intermediate acid chloride).UPLC-MS (Method 2): Rt = 1.06 mm; MS (Elneg) m/z = 284 [M-H].1H-NMR (400 MHz, DMSO-d6): oe [ppm] = 2.36 (s, 3H), 7.28 (s br, 2H), 7.41 (dd,1H), 7.51 (t, 1H), 7.81 (dd, 1H), 9.82 (s, 1H).
The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
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