関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | Benzene, 1-bromo-3-iodo- | HCID 11561 | — |
| 反応物 | 3-Butyn-1-OL | HCID 13566 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 4-(3-Bromophenyl)but-3-yn-1-ol | HCID 21895442 | 92% |
反応手順
A solution of 10.0 gm (35.3 mmol) of 3-iodo-bromobenzene in DMF was treated with 2.95 mL (88 mmol) of 4-butyne-1-ol, 0.2 gm (1.06 mmol) of copper (I) iodide, 1.23 gm of dichlorobis(triphenylphosphine)-palladium(II), and 49 mL (0.35 mol) of triethylamine, stirred at room temperature for 18 h, poured into water and extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried over Na2SO4 and concentrated at reduced pressure. Chromatography of the resultant concentrate on silica gel with a gradient of 5% to 30% EtOAc-hexanes afforded 4-(3-bromophenyl)but-3-yn-1-ol as an orange oil, 7.3 gm (92% yield); 1H NMR (400 MHz, CDCl3) δ: 1.79 (s, 1H), 2.67 (t, 2H, J=6.3 Hz), 3.80 (t, 2H, J=6.3 Hz), 7.14 (t, 1H, J=7.9 Hz), 7.30 (d, 1H, J=7.9 Hz), 7.41 (m, 1H), 7.54 (t, 1H, J=1.6 Hz).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07423158B2 |
|---|
| 出典データセット | uspto-grants-2008_09 |
|---|
| ORD ID | ord-cbe3e1baed484ad6aa1b66bc899ccbd9 |
|---|
| 出典メモ | uspto-grants-2008_09 |
|---|
