Ethyl cyanoacetate → Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoate

HRID 924694

Reaktionsgleichung

Reaktionsgleichung von HRID 924694
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].N1CCCCC1>C1(C)C=CC=CC=1>[CH2:16]([O:15][C:13](=[O:14])[C:12]([C:10]#[N:11])=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:17]

Komponenten

5

Edukt 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 707414-Bromobenzaldehyde

Produkt 1

HCID 367501Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Bromobenzaldehyde (3 g, 16.21 mmol) and ethyl cyanoacetate (1.9 ml, 17.84 mmol) in toluene was added piperidine (27 μl) and the reaction mixture was refluxed for 1 hour with a Dean-Stark separator. The solvent was removed under reduced pressure, the residue triturated with warm ethyl acetate, filtered to yield the desired product as a yellow solid (4.03 g, 89% yield). LC/MS: (PS-A2) Rt 3.44.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 1 hour with a Dean-Stark separator
  2. customThe solvent was removed under reduced pressure
  3. customthe residue triturated with warm ethyl acetate
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-3dff0bbeba674f4fb50376763819fae3
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283226B2

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