Dimethylformamide → 4-(3,4-dimethoxy-2-(methoxymethoxy)phenyl)isobenzofuran-1(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3,4-dimethoxy-2-(methoxymethyl)phenylboronic acid (compound 301)(2.3 g, 10.79 mmol) in dimethylformamide (25 mL) under nitrogen atmosphere, were added cesium carbonate (10.52 g, 32.31 mmol), tetrakis(triphenylphosphine)palladium(0) (623 mg, 0.539 mmol) and 4-bromoisobenzofuran-1(3H)-one (5.2 g, 21.5 mmol) and the resultant reaction mixture was heated to 80° C. for 3 h. The reaction mixture was filtered off and the filtrate was extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-30% ethyl acetate in pet ether) afforded 4-(3,4-dimethoxy-2-methoxymethoxy-phenyl)-3H-isobenzofuran-1-one as a solid.

Provenance & Evidence