Aluminum(III) Chloride → HCID 135856719, compound

Participants

Reaction Conditions

Reaction Steps

Treat a stirred solution of 3-(4-methoxyphenyl)thieno[2,3-d]isoxazole (9.10 g, 0.0394 mol) in 1,2-dichloroethane (100 mL) portionwise with aluminum chloride (15.74 g, 0.118 mol). The mixture is stirred at 70° C. for 1.5 hours, cool to room temperature, and decant into a mixture of concentrated hydrochloric acid (50 mL) and ice (160 g). Stir the mixture for 0.5 hour, filter through Celite, separate the phases and extract the filter cake with dichloromethane. Also use the dichloromethane extract to extract the aqueous phase. Combine the organic phases, wash twice with water, dry (Na2SO4), filter and evaporate. Purify the crude material by flash chromatography on silica gel using gradient elution with 1 to 2% methanol in dichloromethane. Concentrate the desired fractions to afford the title compound as a tan solid (7.1 g, 83% yield).

Provenance & Evidence