Cesium carbonate → 5-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one

Participants

Reaction Conditions

Reaction Steps

A stirring solution of 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-isobenzofuran-1-one (2.23 g, 8.58 mmol) in dimethylformamide (30 mL) was purged with argon for 1 h, to this cesium carbonate (8.37 g, 25.74 mmol), Pd(PPh3)4 (495 mg, 0.429 mmol) and 3-bromo-2,6-dimethoxy-phenol (2.0 g, 8.58 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 g, 40.7%).

Provenance & Evidence