関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sodium Iodide | HCID 5238 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 4-Bromo-1,1-difluorobut-1-ene | HCID 2782240 | — |
| 反応物 | 3-((4-(Difluoromethoxy)phenyl)ethynyl)phenol | HCID 59790321 | — |
| 触媒 | Trioctylmethylammonium chloride | HCID 21218 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | Methyl Ethyl Ketone | HCID 6569 | — |
| 生成物 | 1-(4,4-Difluorobut-3-enyloxy)-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene | HCID 59790317 | 46.2% |
反応手順
A mixture of 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol (900 mg), potassium carbonate (636 mg), Aliquat 336 (4 drops), sodium iodide (catalytic) and 4-bromo-1,1-difluoro-1-butene (591 μL) in methyl ethyl ketone was placed in a pressure vessel, heated at 80° C. for 15 h, cooled to room temperature, diluted with dichloromethane and filtered. The filtrate was concentrated in vacuo. The resultant residue was purified by flash chromatography (silica gel, eluant: 2.5% ethyl acetate/hexane to afford 1-(4,4-difluorobut-3-enyloxy)-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene, 560 mg (46.2% yield); 1H NMR (chloroform-d1): δ 7.51 (d, J=8.8 Hz, 2H), 7.24 (m, 1H), 7.10 (m, 1H), 7.08 (d, J=8.8 Hz, 2H), 7.03 (m, 1H), 6.87 (m, 1H), 6.52 (t, J=73.5 Hz, 1H), 4.32 (m, 1H), 3.97 (t, J=6.4 Hz, 2H) and 2.47 (m, J=6.4 Hz, 2H); MS (ES pos) m/z 350.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07423158B2 |
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| 出典データセット | uspto-grants-2008_09 |
|---|
| ORD ID | ord-04f34b7d441e4224abcdfc90649b95ba |
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| 出典メモ | uspto-grants-2008_09 |
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