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
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6-bromo-4-chloro-2-(2-methoxyphenyl)quinazoline (0.14 g, 0.4 mmol) in CH2Cl2 (mL) was cooled in a dry ice/acetone bath. A solution of 1.0 M BBr3 in CH2Cl2 (1.2 mL, 1.2 mmol) was slowly added. The cooling bath was removed, and the reaction was stirred at room temperature for 2 h. The reaction was diluted with CH2Cl2 and made basic with a saturated NaHCO3 solution. The organic layer was separated, washed with water, dried over Na2SO4, and evaporated to give 6-bromo-4-chloro-2-(2-hydroxyphenyl)quinazoline (0.15 g).