Dimethyl Sulfate → Methyl 1-methoxy-4-bromo-2-naphthoate

HRID 46218

Reaktionsgleichung

Reaktionsgleichung von HRID 46218
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([OH:15])=O)[CH:3]=1.S([O:21][CH3:22])(OC)(=O)=O.[C:23]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:23])=[C:4]([C:13]([O:21][CH3:22])=[O:15])[CH:3]=1

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 2893934-Bromo-1-hydroxynaphthalene-2-carboxylic acid2×

Produkt 1

HCID 12084039Methyl 1-methoxy-4-bromo-2-naphthoateAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 4-bromo-1-hydroxy-2-naphthoic acid (compound 67, 24.7 g, 92.2 mmol), dimethyl sulfate (21.8 mL, 231 mmol), and K2CO3 (31.9 g, 231 mmol) in acetone (200 mL) was refluxed overnight. The solid was filtered, and the filtrate was condensed to give a solid residue, which was recrystallized from EtOAc/hexanes to afford the title compound (21.4 g, 78%) as a white solid.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. filtrationThe solid was filtered
  3. customcondensed
  4. customto give a solid residue, which
  5. customwas recrystallized from EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b799a19433b34ef4a7ca626fb9a3a390
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541380B2

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