Sodium Bicarbonate → 4-Bromo-2-benzofuran-1[3H]-one

Participants

Reaction Steps

To a stirring solution of 3-Bromo-2-methyl-benzoic acid methyl ester (500 mg, 2.22 mmol) in carbon tetrachloride (6 mL) at 0° C., was added chromylchloride (0.36 mL, 4.45 mmol) and the reaction mixture was heated to reflux for 20 h. The reaction mixture was cooled to RT, added ice water and sat sodium bicarbonate solution at 0° C. 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, 0-10% ethyl acetate in pet. ether) afforded 4-bromo-3H-isobenzofuran-1-one as a solid.

Provenance & Evidence