Hydrochloric Acid → 4-Hydroxy-3,5-diiodobenzoic acid 2-iodobenzyl Ester

Participants

Reaction Steps

A suspension of 3,5-diiodo-4-hydroxybenzoic acid (1 95 mg, 0.5 mmol, 2-iodo benzyl chloride (320 mg, 1.25 mmol), and cesium carbonate (490 mg, 1.5 mmol) in 5 mL DMF was stirred for 15 hours at room temperature. The mixture was then poured into 1 M HCl (100 mL) and a white precipitate formed. The precipitate was isolated filtration and was recrystallized from hot isopropanol/chloroform, yielding the title compound as bright white crystals (140 mg, 61%). 1H NMR (400 MHz, CDC13): δ 8.40 (s, 2H), 7.90 (dd, J=8.0, 1.2 Hz, 1H), 7.44-7.36 (m, 2H), 7.06 (td, J=8.0, 2.0 Hz, 1H), 6.14 (s, 1H), 5.35 (s, 2H).

Provenance & Evidence