Water → 1-Bromo-4-(2-butoxyethoxy)benzene

HRID 1978693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978693
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:15][CH2:16][CH2:17][CH3:18].O>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][O:9][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 991682-(p-Bromophenoxy)ethanol

Produkt 1

HCID 111848761-Bromo-4-(2-butoxyethoxy)benzeneAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In DMF (150 ml) was dissolved 2-(4-bromophenoxy)-1-ethanol (15.7 g). To the mixture was added under ice-cooling 65% sodium hydride (4.3 g),and the mixture was stirred at room temperature for 2 hours. To the mixture was added dropwise iodobutane (17.3 g), and the mixture was stirred for 2 hours. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1) to give 1-bromo-4-(2-butoxyethoxy)benzene (12.6 g).

Aufarbeitung

  1. additionTo the mixture was added under ice-
  2. stirringthe mixture was stirred for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-68b1e8a2020c4591abbcbbc54a8c7028
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235771B1

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