Water → Methyl 3-methyl-5-phenylthiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

At room temperature, a solution of 4-iodobenzene (9.6 mmol) and methyl 3-methylthiophene-2-carboxylate (19.2 mmol) in dimethylacetamide (20 ml) were degassed with nitrogen for 15 minutes. Potassium acetate (0.87 mmol) and palladium acetate (0.02 mmol) were added, the reaction vessel was sealed and heated at 150° C. for 1 hour. Then, the reaction mixture was cooled down to room temperature and poured into water, extracted with dichloromethane, washed with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified by chromatography on silica gel (eluent: gradient of 3% diethyl ether in petroleum ether) to give 100 mg of Intermediate V.1 (22%) as a yellow solid, which was characterized by the following spectroscopic data: 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.57 (s, 3H), 3.88 (s, 3H), 7.13 (s, 1H), 7.32-7.34 (m, 3H), 7.59-7.64 (m, 2H); and MS (ESI, EI+) m/z=233 (MH+).

Provenance & Evidence