Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Hydrochloric Acid | HCID 313 | — |
| Edukt | Toluene | HCID 1140 | — |
| Edukt | Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoate | HCID 367501 | — |
| Edukt | HCID 178478191 | HCID 178478191 | — |
| Produkt | HCID 86654323 | HCID 86654323 | 91% |
Reaktionsschritte
A solution of 3-(4-bromo-phenyl)-2-cyano-acrylic acid ethyl ester (1.5 g, 5.36 mmol) in dry toluene (12 ml) was added dropwise to 4-chlorophenylmagnesium bromide (0.5 M solution in tetrahydrofuran, 6.96 ml, 6.96 mmol) at 0° C. The reaction mixture was heated to 85° C. for 3 hours, poured onto ice, acidified with 1N HCl and extracted with ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated, the crude product was purified over flash silica chromatography eluting with petroleum ether to ethyl acetate/petroleum ether (5:95) to afford the desired product (1.91 g, 91% yield). LC/MS: (PS-A2) Rt 3.78 [M+H]− 391.93.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08247576B2 |
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| Quelldatensatz | uspto-grants-2012_08 |
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| ORD ID | ord-3e3e21ab170d41c7a5c51f7e0b7c237d |
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| Quellennotiz | uspto-grants-2012_08 |
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