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

HRID 365355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 365355
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].[H-].[Na+].Br[CH2:14][O:15][CH3:16]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:14][O:15][CH3:16]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 148270371-Bromo-4-methoxy-2-(methoxymethoxy)benzeneAusbeute 106,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1-Bromo-2-hydroxy-4-methoxybenzene (5.00 g, 24.60 mmol) in DMF was added 60% sodium hydride (1.97 g, 49.20 mmol) at 0° C. under argon. The mixture was allowed to stir at 0° C. for 15 minutes, then 90% bromomethyl methylether (4.10 g, 29.50 mmol) was added. After stirring for 1 h at 0° C. the reaction was quenched with water. The mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent afforded the title compound as an oil (6.5 g, quantitative yield). 1H NMR (400 MHz, CDCl3) δ 7.41 (d, 2H), 6.76 (d, 1H), 6.47 (dd, 1H), 5.24 (s, 2H), 3.87 (s, 3H), 3.53 (s, 3H).

Aufarbeitung

  1. stirringAfter stirring for 1 h at 0° C. the reaction
  2. customwas quenched with water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-0cd264c8315b4a22b5e121824522d7bb
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127371

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