Water → methyl 2-bromo-4-(3,4-dichlorophenyl)-6-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate

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Reaction Conditions

Reaction Steps

A mixture of methyl (2Z)-2-[(5-bromo-2-thienyl)carbonyl]-3-(3,4-dichlorophenyl)acrylate (36.64 g, 87.22 mmol) and aluminum trichloride (14.0 g, 105 mmol) in 1,2-dichloroethane (687.2 mL) was heated at 80° C. under argon overnight. The mixture was then cooled to rt and water (20.4 mL) was added. The mixture was stirred for 30 min and then dryloaded on silica gel. Purified on two ISCO columns, 400 g, EtOAc in hex, 0-80% to afford the product as a yellow solid (31.6 g, 81.3%). LCMS: (AA) ES−: 417, 419. 1H NMR (400 MHz, CDCl3) δ 7.42 (d, J=8.3 Hz, 1H), 7.24 (d, J=2.1 Hz, 1H), 7.02-6.94 (m, 2H), 4.88 (d, J=3.5 Hz, 1H), 3.83 (s, 3H), 3.76 (d, J=3.5 Hz, 1H).

Provenance & Evidence