関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | 1,4-Dibromobenzene | HCID 7804 | — |
| 反応物 | Trimethylsilylacetylene | HCID 66111 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418397 | HCID 178418397 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 1,4-Bis[(trimethylsilyl)ethynyl]benzene | HCID 522492 | 92% |
反応手順
40 mL THF was transferred to a flame-dried Schlenk flask. 1,4-dibromobenzene (2.5 mmol, 0.060 g), Pd(PPh3)4 (0.1 mmol 0.12 g), and CuI (0.2 mmol, 0.004 g) were added. Trimethylsilylacetylene (6 mmol, 0.87 mL) and 10 mL DIPA was added via syringe. The mixture was heated to 45° C. for 24 hrs. under nitrogen. The resulting suspension was filtered and filtrate was concentrated under reduced pressure. The residual solid was dissolved in dichloromethane and washed with an aqueous ammonium chloride solution. The organic layer was concentrated and crude product was subjected to column chromatography (silica, hexanes) to afford a white solid (2.3 mmol, 0.61 g, 90% yield). 1H NMR (400 MHz, CDCl3) δ: 7.37 (s, 4H), 0.22 (s, 18H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09234003B2 |
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| 出典データセット | uspto-grants-2016_01 |
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| ORD ID | ord-1f8f9d829e824e3b966d7709d0fd338e |
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| 出典メモ | uspto-grants-2016_01 |
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