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1-Bromo-2-fluorobenzene → 5-(2-Fluorophenyl)pent-4-yn-1-ol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1-Bromo-2-fluorobenzene | HCID 61259 | — |
| 反応物 | 4-Pentyn-1-ol | HCID 79346 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418397 | HCID 178418397 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 生成物 | 5-(2-Fluorophenyl)pent-4-yn-1-ol | HCID 86687856 | — |
反応手順
1-Bromo-2-fluorobenzene [1072-85-1] (3.0 g, 17 mmol, 1.0 equiv) and pent-4-yn-1-ol [5390-04-5] (2.3 mL, 25 mmol, 1.5 equiv) were dissolved in acetonitrile (40 mL). CuI (0.13 g, 0.68 mmol, 0.04 equiv) and TEA (3.4 mL, 25 mmol, 1.5 equiv) was added to the stirred solution followed by tetrakis(triphenylphosphine)palladium(0) (0.39 g, 0.34 mmol, 0.02 equiv). The solution was heated at reflux for 16 hours. The solution was cooled, filtered through Celite, the Celite pad rinsed with EtOAc and the solvent removed by rotoevaporation. Column chromatography (9:1 hexanes:ethyl acetate) of the residue afforded pure 5-(2-fluorophenyl)pent-4-yn-1-ol Intermediate 60 (1.3 g, 43%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08828973B2 |
| 出典データセット | uspto-grants-2014_09 |
| ORD ID | ord-aba1e866d2cd413daa1a31e8afd20c22 |
| 出典メモ | uspto-grants-2014_09 |