49713-56-6

4-Hydroxy-6-trifluoromethylquinoline (50 mg, 0.2 mmol) was used as starting material and synthesized with reference to the method reported in Bioorganic & Medicinal Chemistry Letters, 2005, 15(4), 1015-1018. The raw material was added to phosphorus trichloride (108 mg, 0.7 mmol). After the addition was completed, the reaction mixture was heated to 90 °C and stirred continuously for 2 hours. Upon completion of the reaction, the pH was adjusted to 8-9 by slow dropwise addition of saturated sodium bicarbonate solution.Subsequently, extraction was carried out with ethyl acetate (30 mL x 3). The organic phases were combined and concentrated under reduced pressure to afford the target product 4-chloro-6-(trifluoromethyl)quinoline (60 mg, colorless oil), which could be used directly in the subsequent reaction without further purification.

[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 4, p. 1015 - 1018
[2] Patent: KR2016/6207, 2016, A. Location in patent: Paragraph 0188; 0191-0194
[3] Patent: US2016/108035, 2016, A1. Location in patent: Paragraph 0136-0137