関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Trimethylsilylacetylene | HCID 66111 | — |
| 反応物 | 3-Bromo-2-iodo-5-(trifluoromethyl)aniline | HCID 57546142 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Triethylamine | HCID 8471 | — |
| 生成物 | 3-Bromo-5-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline | HCID 57546201 | — |
反応手順
3-Bromo-2-iodo-5-(trifluoromethyl)aniline (18.7 g, 51.1 mmol) was dissolved in triethylamine (400 mL). To this was added dichlorobis(triphenylphosphine)palladium(II) (3.59 g, 5.11 mmol), copper(I) iodide (0.973 g, 5.11 mmol), and trimethylsilylacetylene (5.52 g, 56.2 mmol). The reaction was stirred for 2 h at ambient temperature, at 80° C. for 2 h, and then evaporated. The residue was purified by chromatography on silica gel with 5% ethyl acetate/hexanes to give 10.67 g (62.1%) as a brown liquid. 1H-NMR (CDCl3, 400 MHz) δ 7.13 (s, 1H), 6.82 (s, 1H), 4.52 (bs, 2H), 0.29 (s, 9H); LC/MS (HPLC method 4): tR=4.208 min, 336.05(MH)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08026257B2 |
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| 出典データセット | uspto-grants-2011_09 |
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| ORD ID | ord-007ea7fb7a5d426b94102d884d1b418c |
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| 出典メモ | uspto-grants-2011_09 |
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