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1,2-Dibromoethane → 1-(3-Chlorophenyl)cyclopropanecarbonitrile
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1,2-Dibromoethane | HCID 7839 | — |
| 反応物 | m-Chlorophenylacetonitrile | HCID 73722 | — |
| 触媒 | Tetrabutylammonium Iodide | HCID 67553 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 溶媒 | Sodium Hydroxide | HCID 14798 | — |
| 生成物 | 1-(3-Chlorophenyl)cyclopropanecarbonitrile | HCID 15185297 | 56.3% |
反応手順
To a solution of 2-(3-chlorophenyl)acetonitrile (3.2 g, 21 mmol) and 1,2-dibromoethane (3 mL, 35 mmol) in toluene (20 ml), 35% sodium hydroxide and tetrabutylammonium iodide (400 mg, 1.3 mmol) were added. The mixture was vigorously stirred at room temperature for 4 hours. The resulting solution was diluted with water and extracted with ethyl acetate. The organic solution was concentrated to afford brown oil. Chromatography on silica gel (hexane/ethyl acetate=5/1) afforded 1-(3-chlorophenyl)cyclopropanecarbonitrile (2.1 g, 56% yield) as light yellow oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07875647B2 |
| 出典データセット | uspto-grants-2011_01 |
| ORD ID | ord-50a83f5ce8a547809609795fe40542b5 |
| 出典メモ | uspto-grants-2011_01 |