Methanol → Methyl 2-bromo-5-iodobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-5-iodobenzoic acid (2-1), 5.0 g, 15.3 mmol, 1.0 equiv) in methanol (45 mL) was added sulfuric acid (1.06 mL, 19.9 mmol, 1.3 equiv). The reaction mixture was stirred for 60 hours at 60° C., then heated to reflux and stirred 24 hours more. The reaction mixture was cooled, partitioned between EtOAc and saturated sodium bicarbonate solution. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organics were dried over anhydrous sodium sulfate, filtered and concentrated to afford the product (2-2) as a white solid. ESI+ MS [M]+ C8H6BrIO2: 340.7 found, 340.9 required.

Provenance & Evidence