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Water → 1-Bromo-3-[2-(4-diethylcarbamoylbenzyl)phenoxy]propane

HRID 895612
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 895612
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]([C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[H-].[Na+].[Br:24][CH2:25][CH2:26][CH2:27]Br.O>O1CCCC1>[Br:24][CH2:25][CH2:26][CH2:27][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][C:9]1[CH:18]=[CH:19][C:6]([C:4](=[O:5])[N:3]([CH2:1][CH3:2])[CH2:20][CH3:21])=[CH:7][CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 223807182-(4-Diethylcarbamoylbenzyl)phenol

Produkt 1

HCID 120503951-Bromo-3-[2-(4-diethylcarbamoylbenzyl)phenoxy]propaneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-(4-Diethylcarbamoylbenzyl)phenol (100 mg) was dissolved in tetrahydrofuran (2 ml), added with sodium hydride (60%, in oil, 21 mg) and stirred at 60° C. for 1.5 hours. The reaction mixture was added with 1,3-dibromopropane (0.18 ml) and stirred at the same temperature for 3 hours. After the reaction mixture was added with water (10 ml) and the layers were separated, the aqueous layer was extracted with dichloromethane (10 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=3:1) to obtain 99 mg of the title compound. Yield: 69%.

Aufarbeitung

  1. stirringstirred at the same temperature for 3 hours
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (10 ml)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-799802a6badc43e7b58bc9bab0040e96
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06916822B2

Notizen zur Reaktion

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