Dimethyl Sulfate → Methyl 7-bromo-3-methoxy-2-naphthoate

HRID 1773545Notes

Reaction equation

HRID 1773545 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7](O)[C:8]([C:12]([OH:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].COS([O:27][CH3:28])(=O)=O>CC(C)=O>[CH3:16][O:14][C:12]([C:8]1[C:7]([O:27][CH3:28])=[CH:6][C:5]2[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=2)[CH:9]=1)=[O:13]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 745032-Naphthalenecarboxylic acid, 7-bromo-3-hydroxy-

Product 1

HCID 14528105Methyl 7-bromo-3-methoxy-2-naphthoateYield 101.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7-bromo-3-hydroxy-naphthalene-2-carboxylic acid (J. Med. Chem. 1990, 33(1), 171) (5.3 g, 19.85 mmol), potassium carbonate (13.7 g, 99.25 mmol) and dimethylsulfate (3.8 mL, 45.66 mmol) in acetone (50 mL) was heated at reflux for 3.5 hours. The reaction mixture was then filtered; the filtrate was treated with water (5 mL) and the resulting mixture was stirred for 10 minutes. The reaction mixture was concentrated under reduced pressure; the residue was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 5.946 g of 7-bromo-3-methoxy-naphthalene-2-carboxylic acid methyl ester without further purifications.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. filtrationThe reaction mixture was then filtered
  4. additionthe filtrate was treated with water (5 mL)
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in dichloromethane
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ff97dfdd19254c0c8b1c4f097a62a479
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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