Hydrochloric Acid → (4-Benzoyl-2,6-diiodophenoxy)-acetic Acid Benzyl Ester

Participants

Reaction Steps

To a solution of (4-hydroxy-3,5-diiodophenyl)-phenyl-methanone (as prepared in Example 6, 2.25 g, 5.0 mmol) and benzyl 2-bromoacetate (1.71 g, 7.5 mmol) in 50 mL DMF was added cesium carbonate (4.1 g, 13 mmol). The resulting suspension was stirred for 15 hours, then the reaction mixture was poured into ˜150 mL 1 M HCl. A pale oil formed, and the supernatant was removed by decantation. The oil was crystallized from hot isopropanol, yielding the title compound as colorless crystals (1.13 g, 38%). 1H NMR (400 MHz, CDCl3): δ 8.18 (s, 2H), 7.77-7.74 (m, 2H), 7.63 (tt, J=7.4, 1.2 Hz, 1H), 7.54-7.50 (m, 2 H), 7.45-7.35 (m, 5H), 5.33 (s, 2H), 4.71 (s, 2H). TLC (4:1 Hex:EtOAc), Rf 0.52. LRMS (EI+) calc'd for [C22H16I2O4+H] 598.9, found 598.8.

Provenance & Evidence