Aluminum(III) Chloride → HCID 21966430, compound

Participants

Reaction Conditions

Reaction Steps

3-Methyl-but-2-enoic acid (3-bromo-4-methyl-phenyl)-isopropyl-amide (Compound 42, 50 g, 161.2 mmol) was dissolved in dichloromethane (800 mL) and the solution was cooled to 0° C. and treated with AlCl3 (75.23 g, 564.2 mmol). The suspension was stirred at 0° C. for 1 hour and at room temperature for 1 hour and the reaction was quenched with ice. After 10% aqueous HCl was added, the layers were separated and the aqueous layer extracted twice with dichloromethane. The combined organic layers were washed with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was filtered by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.38) to give the title compound as an oil:

Provenance & Evidence