[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12]C)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1To a 0.55M solution of 2-chloro-8-methoxyquinazoline in DCM was added boron tribromide (2.2 eq. of a 1.0 M solution in DCM) over 5 minutes at 0° C. The reaction mixture was stirred at ambient temperature for 22 hours, and then cooled to −5° C. for 30 minutes. The precipitate was collected by vacuum filtration and then stirred in ice water for 30 minutes. The solid was collected by vacuum filtration and rinsed with 2-propanol. The off-white solid was dried in a desiccator to give the desired product in 79% yield. ES/MS m/z 181 (MH+).
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