Bromine → HCID 58228464, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dichloroquinoline (5.0 g, 25.4 mmol) and aluminium trichloride (10.0 g, 76.1 mmol) was heated to 120° C. with stirring under a nitrogen atmosphere. Bromine (4.81 g, 30.48 mmol, 1.54 mL) was added dropwise over 0.5 h, and the mixture was then stirred at 120° C. for 1 hour before being cooled to room temperature. A MeOH/water mixture (50 mL, 1:1) was then slowly added and the mixture was concentrated in vacuum. Dichloromethane (500 mL) and water (250 mL) were added, the organic layers were separated and the aqueous fraction was extracted with dichloromethane (2×50 mL). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (150 mL) before being dried, filtered and concentrated. Purification by column chromatography on silica gel (petroleum ether: EtOAc=10:1) gave 5-bromo-2,6-dichloroquinoline (5.7 g, 82%) as a solid. m/z: 275.2 [M+H]+

Provenance & Evidence