Dimethyl Sulfate → Methyl 7-bromo-3-methoxy-2-naphthoate
Reaktionsgleichung
[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]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
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.
Aufarbeitung
- temperaturewas heated
- temperatureat reflux for 3.5 hours
- filtrationThe reaction mixture was then filtered
- additionthe filtrate was treated with water (5 mL)
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutionthe residue was dissolved in dichloromethane
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-ff97dfdd19254c0c8b1c4f097a62a479
- Quelldatensatz
- uspto-grants-2016_02
- Patentnummer
- US09255110B2
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