Boron tribromide → 3-tert-butyl-6-hydroxy-2-methyl-4-phenylisoquinolin-1(2H)-one
Reaktionsgleichung
[C:1]([C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([O:21]C)=[CH:10][CH:9]=2)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[C:1]([C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([OH:21])=[CH:10][CH:9]=2)([CH3:4])([CH3:2])[CH3:3]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a methylene chloride (5 mL) solution of 3-tert-butyl-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one (100 mg, 0.311 mmol) under argon at −70° C. was added boron tribromide (1.0M, 0.934 mL, 0.934 mmol). The contents of the reaction flask were warmed to room temperature and stirred 24 h. Extracted with methylene chloride (3×), then the combined organic extracts were washed with brine and dried with anhydrous sodium sulfate. Filtration followed by evaporation of solvent in vacuo gave a solid which was triturated with ethanol. Recrystallization from ethyl acetate/ethanol afforded the title compound.