Hydrochloric Acid → HCID 86654323, Verbindung

HRID 888565

Reaktionsgleichung

Reaktionsgleichung von HRID 888565
[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:14]#[N:15])=[CH:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)[CH3:2].ClC1C=CC([Mg][Br:25])=CC=1.[ClH:26].[C:27]1(C)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:30]1[CH:31]=[CH:32][C:27]([Br:25])=[CH:28][CH:29]=1)([C:14]#[N:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:26])=[CH:9][CH:8]=1)[CH3:2]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 367501Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoateHCID 178478191HCID 178478191, Verbindung

Produkt 1

HCID 86654323HCID 86654323, VerbindungAusbeute 91 %

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. additionpoured onto ice
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe crude product was purified over flash silica chromatography
  8. washeluting with petroleum ether to ethyl acetate/petroleum ether (5:95)

Quellen und Nachweise

ORD-Eintrag
ord-3e3e21ab170d41c7a5c51f7e0b7c237d
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247576B2

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