Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 3-Chloro-2-methyl-1-propene | HCID 11241 | — |
| Reactant | 1-Bromo-4-ethylbenzene | HCID 15313 | — |
| Reactant | Sodium Sulfate | HCID 24436 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Magnesium | HCID 5462224 | — |
| Catalyst | Iodide Ion | HCID 30165 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Product | HCID 13765240 | HCID 13765240 | — |
Reaction Steps
Under nitrogen atmosphere, tetrahydrofuran (KANTO, 8.1 mL) was added to magnesium (WAKO, 263 mg) and iodide (WAKO, 1 mg), followed with addition of tetrahydrofuran (KANTO, 5.5 mL) solution comprising 1-bromo-4-ethylbenzene (TCI, 2.0 g). The mixture was stirred at room temperature for 30 minutes. The reaction solution was cooled to 0° C. and added with copper iodide (WAKO, 205 mg) and 3-chloro-2-methyl-1-propene (WAKO, 1.32 mL) followed by stirring at room temperature for 1 hour and 30 minutes. The reaction solution was cooled and added with saturated ammonium chloride solution, and further added with sodium sulfate. The reaction mixture was filtered, and concentrated under reduced pressure to obtain a crude product, which was then purified by silica gel column chromatography to obtain the target compound (500 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08039514B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-68679f2e96e84f699064be164b03f55a |
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| Source note | uspto-grants-2011_10 |
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