Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzoyl chloride, 3-nitro- | HCID 8495 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | HCID 58297446 | HCID 58297446 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 86654258 | HCID 86654258 | 6% |
Reaction Steps
To a solution of 2.50 g (6.99 mmol) of 2-bromo-4-(perfluoroethyl)-6-(trifluoromethyl)aniline in 20 ml of pyridine was added 2.72 g (14.7 mmol) of 3-nitrobenzoyl chloride, followed by stirring at 100° C. for 12 hours. To the reaction liquid were added water and ethyl acetate, followed by extraction with ethyl acetate. The organic layer was washed with 1 M hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. To the obtained residue were added THF and an aqueous sodium hydroxide solution, followed by stirring at room temperature for 8 hours. The reaction liquid was extracted/dried in the same manner as described above, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=7:1→5:1) to prepare 0.202 g (yield 6%) of a target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09237745B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-e2e102b2527344a3933a059c4827abb0 |
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| Source note | uspto-grants-2016_01 |
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