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Bromine → 2-Bromo-6-(1,3-dioxoisoindolin-2-yl)hexanoic Acid
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Bromine | HCID 24408 | — |
| 反応物 | 1,3-Dihydro-1,3-dioxo-2H-isoindole-2-hexanoic acid | HCID 78185 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | Sodium Bisulfite | HCID 23665763 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | 2-Bromo-6-(1,3-dioxoisoindolin-2-yl)hexanoic Acid | HCID 13622640 | 91.5% |
反応手順
Combine 6-phthalimidohexanoic acid (12.7 g, 48 mmol) and dry red phosphorous (1.95 g, 63 mmol). Cool in an ice bath and add dropwise bromine (12.7 mL, 246 mmol). Warm to room temperature and then heat to 80° C. After 3 hours, cool the reaction mixture to ambient temperature, pour into water (300 mL) containing sodium bisulfite, and neutralize using solid sodium bicarbonate and extract with diethyl ether (about 150 mL). Acidify the aqueous layer with concentrated hydrochloric acid give a solid. Collect the solid by filtration and dry to give the title compound (15 g, 91.5% yield, 73.2% for both steps).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06544980B2 |
| 出典データセット | uspto-grants-2003_04 |
| ORD ID | ord-4045474ca86c426ca220798070e2b6ac |
| 出典メモ | uspto-grants-2003_04 |