Hydrochloric Acid → 5'-(1-Methylethyl)-5-phenyl[2,2'-bithienyl]

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 0.55 gram (0.0041 mole) of aluminum chloride in 40 ml of methylene chloride was cooled to 0° C., and a solution of 1.0 gram (0.0041 mole) of 5-phenyl[2,2'-bithienyl], 0.9 gram (0.005 mole) of 2-chloropropane in 40 ml of methylene chloride was added dropwise. Upon completion of addition the reaction mixture stirred at 0° C. for 30 minutes, then was allowed to warm to ambient temperature where it stirred for 16 hours. The reaction mixture was poured into a mixture of ice and aqueous 10% hydrochloric acid. The layers were separated and the aqueous phase was extracted with three 25 ml portions of diethyl ether. The organic layers were combined and the combination washed in succession with a solution of aqueous 5% sodium bicarbonate, water, and an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished with 100% hexane. The appropriate fractions were combined and concentrated under reduced pressure to yield 0.7 gram of 5'-(1-methylethyl)-5-phenyl[2,2'-bithienyl]; m.p. 104°-106° C.

Provenance & Evidence