反应详情

温度

-78 °C

6-Bromo-4-chloro-2-(2-methoxyphenyl)quinazoline (393 mg, 1:12 mmol) was dissolved in CH2Cl2 (3 mL), and the flask was flushed with N2. After cooling the reaction mixture to −78° C., 1 M BBr3 in CH2Cl2 (3.37 mL, 3.37 mmol) was added dropwise, then the reaction was slowly warmed to room temperature and stirred-for 2 h. After quenching the mixture with saturated aqueous NaHCO3 (1×), it was transferred into a separatory funnel with CH2Cl2. The organic layer was washed with H2O (2×), dried over Na2SO4, and concentrated. Purification via silica gel chromatography using 0-5% EtOAc and CH2Cl2:hexanes (1:1) gave 2-(6-bromo-4-chloroquinazolin-2-yl)phenol (229 mg, 61%). LC/MS: m/z 335.30 (M+H)+ at 4.18 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

1. customthe flask was flushed with N2
2. temperaturethe reaction was slowly warmed to room temperature and stirred-for 2 h
3. customAfter quenching the mixture with saturated aqueous NaHCO3 (1×), it
4. customwas transferred into a separatory funnel with CH2Cl2
5. washThe organic layer was washed with H2O (2×)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customPurification via silica gel chromatography