Sodium hydride → 1-Bromo-4-methoxy-2-(methoxymethoxy)benzene

HRID 2288161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2288161
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[OH:12].[CH3:13][O:14][CH2:15]Br>CN(C=O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[O:12][CH2:13][O:14][CH3:15]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 134938392-Bromo-5-methoxyphenol

Produkt 1

HCID 148270371-Bromo-4-methoxy-2-(methoxymethoxy)benzeneAusbeute 92.410,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1 -Bromo-4-metboxy-2-methoxymethoxybenzene. To a suspension of NaH (2.5 g, 0.06 mol) in dry DMF (100 mL) at 0° C. was added solution of 1-bromo-2-hydroxy-4-methoxybenzene (10.6 g, 0.05 mol). After stirring at 0° C. for 30 min. bromomethyl methyl ether (7.8 g, 0.06 mmol) were dropwise added. The mixture was warmed to room temperature over 20 min. and then stirred for 2 h, it was then quenched cautiously by the addition of cold dilute HCl and extracted with EtOAc. The EtOAc extract was washed successively with; H2O, 5% aqueous NaHCO3, H2O and finally brine. After drying (MgSO4) filtration and evaporation gave liquid. The product was purified by distillation (85° C., 0.2 mm Hg) to give the title compound as a colorless oil (13.7 g, 97%).

Aufarbeitung

  1. additionwere dropwise added
  2. customit was then quenched cautiously by the addition of cold dilute HCl
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed successively with
  6. customAfter drying
  7. filtration(MgSO4) filtration and evaporation
  8. customgave liquid
  9. distillationThe product was purified by distillation (85° C., 0.2 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-2c1837b2689d4697a95f6487704a966b
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06087389

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