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

HRID 1617502

Reaktionsgleichung

Reaktionsgleichung von HRID 1617502
[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 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-benzaldehyde (5 g) and ethyl cyanoacetate (2.9 mL) in toluene (50 mL) was added piperidine (0.046 mL), and the mixture was stirred at reflux for 2 h with a Dean-Stark separator. The mixture was cooled to rt, stirred overnight and toluene was evaporated in vacuo. The crude residue was crystallized from EtOAc to yield the title compound (6.77 g, 90%) as a light yellow solid, MS (EI): m/z=279 ([M]+, 1Br).

Aufarbeitung

  1. temperatureat reflux for 2 h with a Dean-Stark separator
  2. stirringstirred overnight
  3. customtoluene was evaporated in vacuo
  4. customThe crude residue was crystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-27d9c19a64fc45d4872476ab5d8e54cc
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765730B2

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