Potassium Carbonate → Ethyl 4-(3-bromophenoxy)butanoate

HRID 36153

Reaktionsgleichung

Reaktionsgleichung von HRID 36153
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 76300Ethyl 4-bromobutyrate

Produkt 1

HCID 22407915Ethyl 4-(3-bromophenoxy)butanoateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 7.0 g of 3-bromophenol and 7.8 g of ethyl 4-bromobutyrate in 50 ml of DMF is added 11.2 g of K2CO3. The mixture is heated at 60° C. for 1 day and then poured into an ice-water mixture. This mixture is extracted with ether, and the ether extract is washed with water and dried over MgSO4. After filtration and concentration, a solution of 9.3 g of the ethyl 4-(3-bromophenoxy)butyrate obtained in 100 ml of THF is cooled to 0° C.; and 130 ml of a 1.5M solution of DIBAL-H in toluene is added dropwise. The reaction is stirred for 1 hour at 0° C. and 2 hours at room temperature, following which the reaction mixture is poured into a mixture of ice/3N HCl and extracted with ether. The ether extract is washed with water and dried over MgSO4. Filtration and concentration yields 4-(3 -Bromophenoxy)butan-1-ol.

Aufarbeitung

  1. extractionThis mixture is extracted with ether
  2. extractionthe ether extract
  3. washis washed with water
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration and concentration

Quellen und Nachweise

ORD-Eintrag
ord-26810b48b3c1469f94b5bd575d02ab24
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05412137

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