Ethanol → 4-Amino-2-(trifluoromethoxy)phenol

Temperature

50 °C

223 mg (1.0 mmol) of 4-nitro-2-trifluoromethoxyphenol, 224 mg (4.0 mmol) of reduced iron powder, and 321 mg (6.0 mmol) of ammonia chloride were successively added to a mixture of 20 mL of ethanol and 6.0 mL of water under argon atmosphere with mechanical stirring. The mixture was slowly heated to 50° C. and allowed to react at this temperature for 1.5 h until the solution turned brown. The reaction was stopped, naturally cooled, filtered under reduced pressure, and the filter cake was washed with 10 mL of ethyl acetate. 20 mL of water and 20 mL of ethyl acetate were added to the filtrate. The organic layer was isolated, and the water layer was extracted with 20 mL×2 of ethyl acetate. The organic layers were combined, successively washed with 50 mL of water and 50 mL of saturated saline, dried over anh. MgSO4, filtered and concentrated to obtain 144 mg of a dark red solid. Yield 74.4%.

1. customto react at this temperature for 1.5 h until the solution
2. temperaturenaturally cooled
3. filtrationfiltered under reduced pressure
4. washthe filter cake was washed with 10 mL of ethyl acetate
5. addition20 mL of water and 20 mL of ethyl acetate were added to the filtrate
6. customThe organic layer was isolated
7. extractionthe water layer was extracted with 20 mL×2 of ethyl acetate
8. washsuccessively washed with 50 mL of water and 50 mL of saturated saline
9. dry with materialdried over anh. MgSO4
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-da447fb67b624efea2d9a0a037aef0fa

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604065B2