Boron tribromide → 2-Chloro-6-hydroxyquinoline-3-carbaldehyde
Reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14]C)[CH:8]=2)[N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:14])[CH:8]=2)[N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (5.27 g, 23.8 mmol) in anhydrous CH2Cl2 (180 mL) in a 500 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise BBr3 (71.3 mL, 71.3 mmol) at 0° C. and the mixture was stirred at RT overnight. The mixture was then added dropwise to a water/ice mixture, and the solid was filtered and dried under vacuum to give 2-chloro-6-hydroxyquinoline-3-carbaldehyde SLA 47016 as a yellow solid (3.14 g, 64% yield).