Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Bromide | HCID 6332 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 4-Hydroxy-3-Nitroacetophenone | HCID 138723 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 12306485 | HCID 12306485 | 96% |
Reaction Steps
To a solution of 4′-hydroxy-3′-nitroacetophenone (1.0 g, 5.5 mmol) in anhydrous DMF (20 mL) was added anhydrous K2CO3 (3.0 g, 22 mmol) and then bromoethane (0.49 mL, 6.6 mmol). After heating at 80° C. for 20 h, the reaction mixture was cooled, combined with saturated aqueous NH4Cl (50 mL) and extracted with Et2O (2×100 mL). The combined organic layers were washed with water (3×50 mL), 1 N NaOH (50 mL) and then brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to afford the title compound (1.1 g, 96%) as a light brown solid, which was used without further purification. 1H-NMR (CDCl3): δ 8.41 (1H, d), 8.15 (1H, dd), 7.14 (1H, d), 4.28 (2H, q), 2.61 (3H, s), 1.52 (3H, t).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07115640B2 |
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| Source dataset | uspto-grants-2006_10 |
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| ORD ID | ord-9ed639c29de3453ba30076f466f6abc0 |
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| Source note | uspto-grants-2006_10 |
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