1,2-Dichloroethane → trans-methyl 2-bromo-4-(4-chlorophenyl)-6-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a 500 mL round bottom flask was added a solution of methyl (2Z)-2-[(5-bromo-2-thienyl)carbonyl]-3-(4-chlorophenyl)acrylate (6.26 g, 16.2 mmol), in 1,2-dichloroethane (210.0 mL, 2665.4 mmol). Aluminum trichloride (2.164 g, 16.23 mmol) was added and the reaction mixture was heated to 80° C. and allowed to stir for 18 hours. The reaction was cooled to ambient temperature and concentrated under reduced pressure. The crude material was dry loaded onto silica gel and then purified using a ISCO (40 g cartridge, gradient hexanes to 30% EtOAc over 30 min) to afford the title compound (3.96 g, 60%) as a brown oil. LC/MS (AA) ES− 385, 387, 389. 1H NMR (dmso-d6, 400 MHz): δ 7.43-7.29 (m, 5H), 4.91 (d, 1H), 4.04 (d, 1H), 3.71 (s, 3H).

Provenance & Evidence