Hydrochloric Acid → HCID 21969394, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence