Aluminum(III) Chloride → HCID 58245834, compound

Participants

Reaction Steps

A solution of ethyl 2-(5-bromothiophene-2-carbonyl)-3-phenylacrylate (1.3 g, 3.56 mmol) and aluminum trichloride (0.563 g, 4.27 mmol) in nitroethane (20 ml) was heated at 83° C. for 2.75 hours. The reaction mixture was poured into 1N HCl-ice solution, and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4) and concentrated to give a brown oil. The crude product was purified by silica gel flash chromatography using 0-5% ethyl acetate in hexanes to give ethyl 2-bromo-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate as a viscous foam (1.024 g, 78.8% yield). LCMS m/z 366, 368 (M+1); 388.9, 386.9 (M+23); HPLC: Rt 3.438, 3.718 min.

Provenance & Evidence