Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene | HCID 2733265 | — |
| Reactant | 4-Amino-3-fluorophenol | HCID 2735919 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 53465158 | HCID 53465158 | 89% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08759531B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-91afce51a01442f2a7bca52ec639330d |
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| Source note | uspto-grants-2014_06 |
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