Hydrochloric Acid → 3,5-Diiodo-4-(3-bromobenzyloxy)benzoic Acid

Participants

Reaction Steps

A 1.2 M solution of lithium hydroxide (0.5 mL, 0.6 mmol) was added to a solution of 4-(3-bromo-benzyloxy)-3,5-diiodo- benzoic acid 3-bromo-benzyl ester (as prepared in Example 1, 363 mg, 0.5 mmol) in 4 mL THF. The biphasic solution was stirred for 17 hours, after which time the reaction mixture was poured into 1 M HCl (15 mL). The resulting white precipitate was isolated by filtration, rinsed with water, and dried in vacuo, yielding the title compound as a white powder (270 mg, 97%). 1H NMR (400 MHz, DMSO-d6): δ 13.39 (br. s, 1H), 8.33 (s, 2H), 7.81 (s, 1H), 7.63-7.61 (m, 2H), 7.44 (appar. t, J=7.8 Hz, 1H), 5.00 (s, 2H). HPLC (30-90), 17.20 min. LRMS (EI−) calc'd for [C14H9BrI2O3—H] 556.8, found 556.6.

Provenance & Evidence