Ethanol → HCID 11310424, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-1-indanone (0.52g, 2.5 mmol) in toluene (5 mL) were added tetrakis(triphenylphosphine)-palladium(0) (29 mg, 0.03 mmol), thiophene-2-boronic acid (0.48 g, 3.7 mmol), ethanol (5 mL), and 2.0 N sodium carbonate (3 mL). The solution was flushed with nitrogen for 3 minutes. The reaction was heated at 110-120° C. for 4 h. Reaction cooled to room temperature and diluted with ethyl acetate (200 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (2×50 mL), water (40 mL), saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered and concentrated to afford 5-(2-thienyl)-2,3-dihydro-1H-inden-1-one (0.50g, 94% yield) as pure solid product. 1H NMR (400 MHz, CDCl3) 7.80 (d, 1H), 7.70 (s, 1H), 7.62 (d, 1H), 7.43 (dd, 1H), 7.38 (dd, 1H), 7.12 (m, 1H), 3.20 (m, 2H), 2.66 (m, 2H).

Provenance & Evidence