Hydrochloric Acid → 1-(2-Bromo-ethoxy)-2-methoxy-4-methyl-benzene

HRID 734401

Reaktionsgleichung

Reaktionsgleichung von HRID 734401
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[OH:10].[H-].[Na+].[Br:13][CH2:14][CH2:15]Br.Cl>CN(C=O)C>[Br:13][CH2:14][CH2:15][O:10][C:4]1[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:3]=1[O:2][CH3:1]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 71442-Methoxy-4-MethylphenolHCID 78391,2-DibromoethaneHCID 24758Sodium hydride

Produkt 1

HCID 246891991-(2-Bromo-ethoxy)-2-methoxy-4-methyl-benzeneAusbeute 25,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 2-methoxy-4-methylphenol (1000 mg, 7.24 mmol) in DMF (40 mL) at rt was added sodium hydride (60% dispersion in mineral oil, 579 mg, 14.48 mmol). The reaction mixture was stirred for 1 h, then 1,2-dibromoethane (6.80 g, 136.18 mmol) was added. The resulting solution was heated at 50° C. for 24 h, then cooled to rt. The solution was treated with 2N HCl and extracted with EtOAc. The combined extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography using a step gradient of 30 and 50% EtOAc/hexanes to give the title compound as a white solid (460 mg, 24%). GC/MS (EI) m/z 244 (M)+, RT 7.40 min.

Aufarbeitung

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2015f34f08bf4d0b87f94842d4580eef
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592361B2

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