Cesium carbonate → 5-(4-(difluoromethoxy)-3-methoxy-2-(methoxymethoxy)phenyl)isobenzofuran-1(3H)-one

Participants

Reaction Conditions

Reaction Steps

A stirring solution of 1-bromo-4-(difluoromethoxy)-3-methoxy-2-(methoxymethoxy)benzene (3 g, 9.58 mmol) in N,N-dimethylformamide (30 mL) was purged with argon for 1 h, to this cesium carbonate (9.36 g, 28.74 mmol), tetrakis(triphenylphosphine) palladium(0) (553 mg, 0.479 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isobenzofuran-1(3H)-one (2.98 g, 11.49 mol) were added and the resultant reaction mixture was heated to 90° C. for 4 h. The reaction mixture was cooled to RT, filtered 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, 0-20% ethyl acetate in pet ether) afforded 5-(4-(difluoromethoxy)-3-methoxy-2-(methoxymethoxy)phenyl)isobenzofuran-1(3H)-one as a solid (1.5 g, 42%).

Provenance & Evidence