Methanol → Methyl 3-acetyl-5-bromo-4-hydroxybenzoate
Reaktionsgleichung
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([Br:14])[C:12]=1[OH:13])[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].S(Cl)(Cl)=O.[CH3:19]O>>[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([Br:14])[C:12]=1[OH:13])[C:7]([O:9][CH3:19])=[O:8])(=[O:3])[CH3:2]Komponenten
4
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a stirred suspension of 3-acetyl-5-bromo-4-hydroxybenzoic acid (240 g, 926 mmol) in MeOH (2 L) was added dropwise sulfurous dichloride (68 mL, 926.5 mmol) under nitrogen and the mixture was heated at 80° C. for 3 h. The reaction mixture was cooled to room temperature concentrated, diluted with DCM. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated to afford a crude compound, which was purified on silica, eluting with 70% of DCM in petroleum ether. The solvents were evaporated to dryness to afford methyl 3-acetyl-5-bromo-4-hydroxybenzoate (108 g, 42.7%) as a white powder. Mass Spectrum: m/z [M−H]−=229.