Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 118022659 | HCID 118022659 | — |
| Catalyst | Iron | HCID 23925 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 61718883 | HCID 61718883 | 99.4% |
Reaction Steps
A mixture of 2-bromo-1-(cyclopropylmethoxy)-4-nitrobenzene (1.07 g, 3.9 mmol), ammonium chloride (421 mg, 7.8 mmol), and iron powder (1.1 g, 20 mmol) suspended in THF (6.5 mL), water (2.5 mL) and ethanol (6.5 mL) was heated to 95° C. using microwave irradiation (normal) for 3 h. The crude reaction mixture was filtered through a short plug of celite; the celite plug was washed with MeOH (˜10 mL). The resulting filtrate was concentrated in vacuo. The resulting residue was diluted with EtOAc (50 ml) and washed with saturated bicarbonate solution (aq), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound, (939 mg, 90%). The material was carried forward without any further purification. LCMS (M+H)+=242.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09034900B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-9b3b24bfc8de48d1a362102d9b8df6f3 |
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| Source note | uspto-grants-2015_05 |
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