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

HRID 46218

Reaction equation

HRID 46218 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 12084039Methyl 1-methoxy-4-bromo-2-naphthoateYield 78.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-b799a19433b34ef4a7ca626fb9a3a390
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Linked notes

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