Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Sodium chlorodifluoroacetate | HCID 2734985 | — |
| Reactant | 5-Bromo-2-hydroxybenzonitrile | HCID 2757014 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 79018268 | HCID 79018268 | 61.3% |
Reaction Steps
Sodium chloro(difluoro)acetate (9.62 g, 63.1 mmol) and cesium carbonate (12.3 g, 37.9 mmol) were added to a mixed solution of 5-bromo-2-hydroxybenzonitrile (5.00 g, 25.2 mmol) in DMF (50 mL) and water (5 mL), and the mixture was stirred at 100° C. for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-98/2] to obtain the title compound (3.83 g, yield: 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150575B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-5bf2bfb8721344f8aa8ca2ac7ca4c0df |
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| Source note | uspto-grants-2015_10 |
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