HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 1,2-Bis(4-methoxyphenyl)ethyne
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | 4-Iodoanisole | HCID 69676 | — |
| Reactant | 1-Ethynyl-4-methoxybenzene | HCID 251020 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1,2-Bis(4-methoxyphenyl)ethyne | HCID 617234 | 95% |
Reaction Steps
To a mixture of 4-ethynylanisole (700 mg, 5.30 mmol), 4-iodoanisole (1.30 g, 5.55 mmol), (PPh3)2PdCl2 (74.4 mg, 0.106 mmol), and CuI (10.1 mg, 0.053 mmol) in THF (7 ml), diisopropyl amine (1.13 g, 11.1 mmol) was added dropwise under ice cooling under argon atmosphere. After stirring at room temperature for 1 h, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water then saturated brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=15/1) to give bis(4-methoxyphenyl)ethyne (95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06838574B1 |
| Source dataset | uspto-grants-2005_01 |
| ORD ID | ord-8e354f6f47b9491e8ee9038da2c0a51a |
| Source note | uspto-grants-2005_01 |