Boron tribromide → 2-Chloro-6-hydroxyquinoline-3-carbaldehyde

Participants

Reaction Steps

To a solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (1.01 g, 4.54 mmol) in dry CH2Cl2 (36 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer at 0° C. under N2 was added dropwise BBr3 (1.0 N solution in CH2Cl2, 13.60 mL, 13.60 mmol). After complete addition, the bath was removed and stirring was continued overnight at RT. The reaction mixture was then added dropwise to a mixture of water and ice (50 mL) under stirring. After complete addition, the mixture was stirred for 30 min at RT and then filtered to give, after drying, 2-chloro-6-hydroxyquinoline-3-carbaldehyde as a yellow solid (0.77 g, 82% yield).

Provenance & Evidence