Calcium Carbonate → Benzoic acid, 4-amino-2-chloro-5-iodo-, methyl ester

Participants

Reaction Steps

To a suspension of compound 22j (1.18 g, 6.38 mmol) and CaCO3 (1.28 g, 12.8 mmol) in MeOH (13 mL) was added a solution of iodine monochloride (1.09 g, 6.70 mmol) in CH2Cl2 (6 mL) dropwise at room temperature. The resulting reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was concentrated and then partitioned between EtOAc and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 20-25% EtOAc/hexanes) to provide methyl 4-amino-2-chloro-5-iodo-benzoate 22k as the major product and methyl 4-amino-2-chloro-3-iodo-benzoate 22l as the minor product.

Provenance & Evidence