Bismuth nitrate → 4-Nitro-2-(trifluoromethoxy)phenol

Temperature

50 °C

3.0 g (7.5 mmol) of anh. bismuth nitrate was added to a solution of 891 mg (5.0 mmol) of 2-trifluoromethoxyphenol in 20 mL of tetrahydrofuran (redistilled) under argon atmosphere with stirring. The mixture was slowly heated to 50° C. and allowed to react at this temperature for 10 min. The reaction was stopped, cooled, filtered under reduced pressure and the filter cake was washed with 20 mL of tetrahydrofuran. The filtrate was concentrated, and 40 mL of water and 45 mL of ethyl acetate were added. The organic layer was isolated, and the water layer was extracted with 40 mL×2 of ethyl acetate. The organic layers were combined, successively washed with 110 mL of water and 110 mL of saturated saline, dried over anh. MgSO4, filtered and concentrated. The residue was purified by silica column chromatography (mobile phase: petroleum ether: ethyl acetate=15:1) to obtain 346 mg of a yellow oil. Yield 31.4%.

1. customto react at this temperature for 10 min
2. temperaturecooled
3. filtrationfiltered under reduced pressure
4. washthe filter cake was washed with 20 mL of tetrahydrofuran
5. concentrationThe filtrate was concentrated
6. addition40 mL of water and 45 mL of ethyl acetate were added
7. customThe organic layer was isolated
8. extractionthe water layer was extracted with 40 mL×2 of ethyl acetate
9. washsuccessively washed with 110 mL of water and 110 mL of saturated saline
10. dry with materialdried over anh. MgSO4
11. filtrationfiltered
12. concentrationconcentrated
13. customThe residue was purified by silica column chromatography (mobile phase: petroleum ether: ethyl acetate=15:1)

ORD record

ord-61c6b4ead3544fd6b03bab1aa7d654e6

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604065B2