Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2,4-Dichlorophenol | HCID 8449 | — |
| Reactant | 1-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-one | HCID 521105 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 60207510 | HCID 60207510 | 55.8% |
Reaction Steps
Potassium t-butoxide (0.30 g, 2.67 mmol) was suspended in anhydrous tetrahydrofuran (25 mL), 2,4-dichlorophenol (0.40 g, 2.43 mmol) was added and the resulting mixture was stirred at ambient temperature under nitrogen for 30 minutes. After this time, 1-(5-chloro-4-nitro-2-thienyl)ethanone (0.5 g, 2.43 mmol) was added, the resulting mixture was stirred at ambient temperature for 45 minutes, then it was poured into water (100 mL) and stirred at ambient temperature overnight. The resulting solid was collected by filtration, washed with water (2×10 mL) and dried in air. The crude product was dissolved in acetonitrile (7 mL), the resulting solution was evaporated to near dryness and the residue was triturated with diethyl ether (2 mL). The resulting solid was collected by filtration and dried in vacuo at 40° C. overnight to afford the title product as a solid (0.45 g, 55% yield). 1H NMR (300 MHz, d6-acetone) δ: 8.15 (1H, s), 7.68 (1H, d), 7.51 (2H, m), 2.45 (3H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680139B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-1ac09b7529c64045bb6a45d8671d5d0d |
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| Source note | uspto-grants-2014_03 |
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