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

HRID 335050

Reaction equation

HRID 335050 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 acid

Product 1

HCID 12084039Methyl 1-methoxy-4-bromo-2-naphthoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-bromo-1-hydroxy-2-naphthoic acid (see Example 1, 1.63 g, 6.10 mmol) in 35 mL of acetone was added dimethyl sulfate (1.75 mL, 18.3 mmol) and potassium carbonate (2.95 g, 21.4 mmol). The reaction was heated to reflux for 14 hours, cooled to room temperature, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes to provide methyl 4-bromo-1-methoxy-2-naphthoate that gave a proton NMR spectra consistent with theory.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 14 hours
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a51ff0d38edf42aba92bee747b035f5f
Source dataset
uspto-grants-2014_11
Patent number
US08883850B2

Linked notes

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