Cesium carbonate → 4-(3-Hydroxy-2,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one

Participants

Reaction Conditions

Reaction Steps

A stirring solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one (3 g, 12.87 mmol) in dimethylformamide (30 mL) was purged with argon for 1 h, to this cesium carbonate (12.58 g, 38.61 mmol), Pd (PPh3)4 (743 mg, 0.64 mmol) and 3-bromo-2,6-dimethoxyphenol (3.32 g, 12.87 mmol) were added and the resultant reaction mixture was heated to 80-90° C. for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was diluted with water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, 0-10% ethyl acetate in pet ether) afforded the title compound as a solid (1.5 g, 41%).

Provenance & Evidence