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4-Toluenesulfonyl chloride → 4-Bromo-1-(toluene-4-sulfonyl)-1H-indole
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | 4-Bromoindole | HCID 676494 | — |
| 触媒 | Tetrabutylammonium hydrogen sulfate | HCID 94433 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 4-Bromo-1-(toluene-4-sulfonyl)-1H-indole | HCID 562869 | 94% |
反応手順
4-Bromoindole (1.24 g, 6.3 mmol), p-toluenesulfonyl chloride (1.32 g, 6.9 mmol) and tetrabutyl-ammonium hydrogen sulfate (42 mg, 0.1 mmol) was dissolved in DCM (50 mL). NaOH 2.5 M aq (6 mL, 15 mmol) was added and the mixture was stirred vigorously for 1 h. Diluted with water and DCM, collected the DCM phase and washed it twice with water, dried and concentrated to give the product as white crystalline material (2.07 g, 5.9 mmol). Yield 94%. MS (ESI+) for C15H12BrNO2S m/z 352 (M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07812017B2 |
| 出典データセット | uspto-grants-2010_10 |
| ORD ID | ord-19adf0d4a9a74c9b8e6b5311acd2efe8 |
| 出典メモ | uspto-grants-2010_10 |