Hydrochloric Acid → HCID 21969394, compound

Temperature

0 °C

A mixture of bromobenzene (373 g) and (R)-2-carbomethoxyaminosuccinic anhydride (1) (90.51 g) in dichloromethane (260 ml) was cooled in ice, and aluminum chloride (174.34 g) was added over 1 minute (exothermic!). The dark red mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. The mixture was poured onto crushed ice, and concentrated hydrochloric acid was added slowly with stirring. Diethylether was added and the mixture was stirred until all of the red-brown material disappeared. The layers were separated, and the aqueous was extracted twice more with diethylether. The combined ether extracts were washed with water and extracted with aqueous sodium carbonate. The combined extracts were washed with diethylether, cooled in ice, and acidified with conc. hydrochloric acid. The acid was extracted 3 times with diethylether. The combined extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave the title compound as a foam, 149.6 g. [α]D =-41° (25° C., CH3OH, c=1.0352).

1. temperaturewas cooled in ice
2. additionThe mixture was poured
3. additionwas added slowly
4. stirringwith stirring
5. stirringthe mixture was stirred until all of the red-brown material
6. customThe layers were separated
7. extractionthe aqueous was extracted twice more with diethylether
8. washThe combined ether extracts were washed with water
9. extractionextracted with aqueous sodium carbonate
10. washThe combined extracts were washed with diethylether
11. temperaturecooled in ice
12. extractionThe acid was extracted 3 times with diethylether
13. washThe combined extracts were washed with brine
14. dry with materialdried (MgSO4)
15. customThe solvent was removed under vacuum

ORD record

ord-7955583c5bff459f9f05038852ac62b2

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06084130