Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Methylphenylacetylene | HCID 136600 | — |
| Reactant | HCID 86592826 | HCID 86592826 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86592825 | HCID 86592825 | — |
Reaction Steps
Methyl[3,5-dibromo-4-(4-hydroxy-3-iodophenoxy)phenyl]propionate (17 mg), 3-tolylacetylene (20 mg) and bis(triphenylphosphine)palladium(II) chloride (2.0 mg), copper(I) iodide (1.0 mg) and triethylamine (1 mL) was stirred at reflux. After 2 hours, the reaction mixture was cooled down, dichloromethane was added and washed once with a saturated solution of aqueous ammonium chloride. The organic phase concentrated and the residue purified on column (silica gel, n-heptane/ethyl acetate 8:2), to give 19 mg of methyl {3,5-dibromo-4-[2-(3-tolyl)-5-benzofuranyloxy]phenyl}propionate as a pale yellow solid mass. 1H-NMR (270 MHz, Acetone-d6): δ 7.68 (s, 2H), 7.53 (dd, 1H), 7.36 (t, 2H), 7.21 (d, 2H), 6.89 (m, 2H), 3.64 (s, 3H), 2.98 (t, 2H), 2.74 (t, 2H), 2.40 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07144909B2 |
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| Source dataset | uspto-grants-2006_12 |
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| ORD ID | ord-093a1d9cf1954763852e1fb517a920cf |
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| Source note | uspto-grants-2006_12 |
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