2,2,2-Trifluoroethanol → 5-Bromo-6-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid

In a 25 mL round-bottomed flask, 5-bromo-6-chloropicolinic acid (433 mg, 1.83 mmol) and powdered potassium hydroxide (411 mg, 7.32 mmol) were combined with DMSO (1.9 ml) to give a colorless solution which was stirred at room temperature for 15 min. 2,2,2-trifluoroethanol (275 mg, 198 μl, 2.75 mmol, Eq: 1.5) was added. The reaction mixture was stirred for 24 h at ambient temperature. Since the reaction was complete, 0.75 extra equivalents of 2,2,2-trifluoroethanol was added and the reaction was stirred 48 h at ambient temperature. The reaction mixture was poured onto 1 M HCl/ice water (1×20 mL), extracted with iPrOAc (2×25 mL). The organic layers were dried over Na2SO4 and filtered, removed under reduced pressure to give the title compound as a white solid after recrystallization from CH2Cl2 and heptane (409 mg, 1.36 mmol, 74.4% yield), MS (EI): m/e=299.9 [M+H]+.

1. customto give a colorless solution which
2. stirringThe reaction mixture was stirred for 24 h at ambient temperature
3. stirringthe reaction was stirred 48 h at ambient temperature
4. extractionextracted with iPrOAc (2×25 mL)
5. dry with materialThe organic layers were dried over Na2SO4
6. filtrationfiltered
7. customremoved under reduced pressure

ORD 기록

ord-bb4dc2b5eb0647ecb024ca7e9493766d

출처 데이터셋

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09290451B2