Potassium Carbonate → 3-Ethyl-4-(4-isopropoxyphenoxy)-1-(3,3-dibromo-2-propenyloxy)benzene

HRID 260774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 260774
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:20])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([CH3:19])[CH3:18])=[CH:12][CH:11]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:27][C:28]([Br:32])=[CH:29][CH2:30]Br>CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[C:5]([O:20][CH2:30][CH:29]=[C:28]([Br:32])[Br:27])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([CH3:19])[CH3:18])=[CH:12][CH:11]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 130414871,1,3-Tribromoprop-1-eneHCID 214662313-Ethyl-4-(4-isopropoxyphenoxy)phenol

Produkt 1

HCID 214663373-Ethyl-4-(4-isopropoxyphenoxy)-1-(3,3-dibromo-2-propenyloxy)benzeneAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a mixture of 0.65 g of 3-ethyl-4-(4-isopropoxyphenoxy)phenol, 0.35 g of potassium carbonate and 10 ml of N,N-dimethylformamide, a solution prepared by dissolving 0.73 g of 1,1,3-tribromo-1-propene in 5 ml of N,N-dimethylformamide was added dropwise at room temperature with stirring. After stirring at room temperature for 12 hours, the reaction solution was poured into ice-water, and extracted twice with 50 ml, of diethyl ether. Then, the ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 0.80 g of 3-ethyl-4-(4-isopropoxyphenoxy)-1-(3,3-dibromo-2-propenyloxy)benzene, yield 71%; nD23.0 1.5761.

Aufarbeitung

  1. customa solution prepared
  2. additionwas added dropwise at room temperature
  3. stirringAfter stirring at room temperature for 12 hours
  4. extractionextracted twice with 50 ml, of diethyl ether
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give a crude product

Quellen und Nachweise

ORD-Eintrag
ord-e2780b10c8a54faf8d3209f959bad961
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530015

Notizen zur Reaktion

Wird geladen…