Water → 4-Iodo-2-phenylbenzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a 0° C. suspension of the 2-phenyl-4-aminobenzoic acid methyl ester prepared in Example 210B (4.54 g, 20 mmol) in 6.0 N HCl (20 mL) and acetone (10 mL) was added dropwise a solution of sodium nitrite (1.66 g, 24 mmol) in a minimum amount of water. After 30 minutes, potassium iodide (6.64 g, 40 mmol) in a minimum amount of water was added dropwise to the reaction mixture. The internal temperature of the reaction mixture was maintained under 5° C. for both additions. The reaction mixture was then stirred at ambient temperature for one hour. The reaction mixture was diluted with ether (200 mL), washed with water, sodium bisulfite (10% aqueous solution), water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography (8% ethyl acetate-hexane) to give 4-iodo-2-phenylbenzoic acid methyl ester (3.98 g, 59%). 1H NMR (300 MHz, CDCl3) δ 7.77 (m, 2H), 7.55 (d, 1H), 7.38 (m, 3H), 7.27 (m, 2H), 3.63 (s, 3H). Ms (CI+): 356 (M+NH4)+.

Provenance & Evidence