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Triethylsilane → 6-(2-Bromo-5-iodobenzyl)-2,3-dihydrobenzo[b][1,4]dioxine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triethylsilane | HCID 12052 | — |
| 反応物 | Trifluoromethanesulfonic acid | HCID 62406 | — |
| 反応物 | Methanone, (2-bromo-5-iodophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)- | HCID 58340798 | — |
| 溶媒 | Trifluoroacetic acid | HCID 6422 | — |
| 生成物 | 6-(2-Bromo-5-iodobenzyl)-2,3-dihydrobenzo[b][1,4]dioxine | HCID 58340830 | 91.2% |
反応手順
To a stirred solution of (2-bromo-5-iodo-phenyl)-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone (30.0 g, 67.4 mmol) in trifluoroacetic acid (100 mL) was added triethylsilane (86.2 mL, 539.3 mmol) followed by triflic acid (6.0 mL, 67.42 mmol) at room temperature. After stirring for 25 min at room temperature, volatiles were evaporated under reduced pressure. The resulting residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution (200 mL×2), water (200 mL), and brine (200 mL), then dried over sodium sulfate, concentrated and purified by silica gel column chromatography to furnish 6-(2-bromo-5-iodo-benzyl)-2,3-dihydro-benzo[1,4]dioxine (26.5 g).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08614195B2 |
| 出典データセット | uspto-grants-2013_12 |
| ORD ID | ord-4705230df03e4b67bca35f5a3e5c2779 |
| 出典メモ | uspto-grants-2013_12 |