Bromine → HCID 58228464, compound

Temperature

120 °C

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]+

1. stirringthe mixture was then stirred at 120° C. for 1 hour
2. temperaturebefore being cooled to room temperature
3. concentrationthe mixture was concentrated in vacuum
4. additionDichloromethane (500 mL) and water (250 mL) were added
5. customthe organic layers were separated
6. extractionthe aqueous fraction was extracted with dichloromethane (2×50 mL)
7. washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (150 mL)
8. custombefore being dried
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification by column chromatography on silica gel (petroleum ether: EtOAc=10:1)

ORD record

ord-cd54ad8813bb4f1d90e581ac189aea18

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399623B2