Boron tribromide → 2-(6-Bromo-4-chloroquinazolin-2-yl)phenol
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18]C)[N:6]=[C:5]2[Cl:20].B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2[Cl:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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)).
Workup
- customthe flask was flushed with N2
- temperaturethe reaction was slowly warmed to room temperature
- customAfter quenching the mixture with saturated aqueous NaHCO3 (1×), it
- customwas transferred into a separatory funnel with CH2Cl2
- washThe organic layer was washed with H2O (2×)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customPurification via silica gel chromatography
Sources & evidence
- ORD record
- ord-139264c516ee428693183756c8552cb3
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928107B2
Reaction notes
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