Boron tribromide → HCID 10263493, compound
Reaction equation
[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16]C)(=[O:4])[CH2:2][CH3:3].B(Br)(Br)Br>ClCCl>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][CH:11]=[CH:10][C:9]=2[OH:16])(=[O:4])[CH2:2][CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Propanoyl-4-chloro-8-methoxyquinoline (32 g) was dissolved in dichloromethane (250 ml), cooled to -78°, and boron tribromide (37 ml) added slowly. The solution was allowed to warm slowly to room temperature overnight, then recooled in ice and quenched cautiously with water. The resulting solid was filtered off and washed with water to give crude 3-propanoyl-4-chloro-8-hydroxyquinoline (115 g crude weight), which was used without further purification.