Boron tribromide → 3-Isobutyryl-4-chloro-8-hydroxyquinoline

Participants

Reaction Steps

A solution of 3-isobutyryl-4-chloro-8-methoxyquinoline (21.1 g, 80 mmol) in dichloromethane (320 ml) was cooled to -10° and boron tribromide (60.13 g, 240 mmol) added dropwise under nitrogen. The solution was allowed to warm to room temperature, and after 16 hours was poured onto crushed ice (500 g). The layers were separated, and the aqueous layer further extracted with dichloromethane. The combined extracts were washed with brine, dried and evaporated to a yellow solid (29.75 g). This complex of 3-isobutyryl-4-chloro-8-hydroxyquinoline was used without further purification.

Provenance & Evidence