Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Cyclopropylacetylene | HCID 138823 | — |
| Edukt | Ethyl 5-bromo-2-chlorobenzoate | HCID 144749 | — |
| Katalysator | Copper iodide | HCID 83717 | — |
| Katalysator | HCID 178418476 | HCID 178418476 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | HCID 90314138 | HCID 90314138 | 103,7% |
Reaktionsschritte
To a solution of ethyl 5-bromo-2-chlorobenzoate (1.9 g) in DMF (12 mL), toluene (0.3 mL), cyclopropylacetylene (714 mg), copper iodide (275 mg), dichloro bis(triphenylphosphine)palladium (1.01 g) and triethylamine (20.1 mL) were added, and the mixture was degassed, stirred at 100° C. under argon atmosphere for 8 hours, and then the reaction mixture was cooled to room temperature and diluted with ethyl acetate. The insoluble material was filtered off on celite. The mother liquor was washed with brine, dried over magnesium sulfate and concentrated. By purification on column chromatography, ethyl 2-chloro-5-(cyclopropylethynyl)benzoate (1.86 g) was obtained as brown oil.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US09216968B2 |
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| Quelldatensatz | uspto-grants-2015_12 |
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| ORD ID | ord-560e49dc0ade4467833eb5257c93f891 |
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| Quellennotiz | uspto-grants-2015_12 |
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