Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | HCID 21864764 | HCID 21864764 | — |
| Catalyst | Iron | HCID 23925 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66892336 | HCID 66892336 | 99.7% |
Reaction Steps
7-Iodo-5-nitro-1-benzofuran (2.5 g, 8.6 mmol) and iron (2.51 g, 45.0 mmol) were added to a round bottom flask. Methanol (25 mL), 1,4-dioxane (25 mL) and ammonium chloride (2.5 g, 46.7 mmol), dissolved in water (50 mL), were added and the mixture was heated at 100° C. for 16 h. The reaction mixture was filtered through Celite and volatiles were evaporated off. The residue was dissolved in a mixture of methanol (10 mL) and DCM (90 mL). This mixture was filtered through a silica plug and the solvent was evaporated yielding 2.22 g (99%) of the title compound as a brown oil. HPLC purity 70%, RT=1.26 min (System A; 10-97% MeCN over 3 min). MS (ESI+) for C8H6INO m/z is 260 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07820675B2 |
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| Source dataset | uspto-grants-2010_10 |
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| ORD ID | ord-3b2b84cec6614fd187b8a111a0334f95 |
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| Source note | uspto-grants-2010_10 |
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