Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | N,N-Dimethylglycine hydrochloride | HCID 75605 | — |
| Reactant | 6-Hydroxybenzofuran | HCID 128844 | — |
| Reactant | 1-Iodo-2-methyl-4-(trifluoromethyl)benzene | HCID 21077909 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 69205339 | HCID 69205339 | — |
Reaction Steps
To a stirred solution of 1-benzofuran-6-ol (309 mg, 2.3 mmol) in dioxane (6 mL) and DMF (12 mL) was added 2-methyl-4-trifluoromethylphenyl iodide (600 mg, 2.3 mmol), copper iodide (108 mg, 0.57 mmol), dimethylglycine hydrochloride (243 mg, 1.7 mmol), and cesium carbonate (1.88 g, 5.8 mmol). The reaction was stirred at 110° C. for 22 h. After cooling to room temperature, solvents were removed in vacuo. The residue was dissolved in ethyl acetate, washed with water and brine, dried and concentrated. The crude product was purified on a silica gel column, eluting with ethyl acetate (0-10%) in hexanes. The final product was collected as a slightly yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07442808B2 |
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| Source dataset | uspto-grants-2008_10 |
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| ORD ID | ord-39cc35e2e9c9463ebdfd5d14a4f53d73 |
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| Source note | uspto-grants-2008_10 |
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