Water → HCID 53465158, compound

At room temperature, 3-fluoro-4-amino-phenol (500 mg, 3.93 mmol, 1 eq) was dissolved in N,N-dimethylformide (3 mL). A solution of 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene (917 mg, 4.13 mmol, 1.05 eq) in dichloromethane (3 mL) was added dropwise. The resulted mixture was stirred at room temperature for 16 h. The mixture was added with water (10 mL) and extracted with ethyl acetate (20 mL). The organic phase was washed with saturated brine (10 mL×3), and dried over anhydrous sodium sulfate. The solvent in the organic phase was removed under reduced pressure, and the resulted solid was refluxed in petroleum ether (15 mL) and ethyl acetate (5 mL) for 2 h. The mixture was cooled to room temperature and filtered to give title compound (1.2 g, purity 98%, yield 89%) as a brown solid.

1. extractionextracted with ethyl acetate (20 mL)
2. washThe organic phase was washed with saturated brine (10 mL×3)
3. dry with materialdried over anhydrous sodium sulfate
4. customThe solvent in the organic phase was removed under reduced pressure
5. temperaturethe resulted solid was refluxed in petroleum ether (15 mL)
6. waitethyl acetate (5 mL) for 2 h
7. temperatureThe mixture was cooled to room temperature
8. filtrationfiltered

ORD record

ord-91afce51a01442f2a7bca52ec639330d

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759531B2