Iodine → HCID 9914226, compound

Participants

Reaction Steps

To a solution of methanesulfonic acid 4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenyl ester (3.00 g, 7.84 mmol), in tetrahydrofuran (31.5 mL), 80% aqueous acetic acid (16 mL) and concentrated sulfuric acid (0.87 mL) was added iodine (1.59 g, 6.27 mmol, 0.8 eq) and iodic acid (0.414 g, 2.35 mmol, 0.9 eq) at room temperature. The mixture was stirred at room temperature for 12 days. The reaction mixture was poured into a dilute aqueous solution of sodium bisulfite (200 mL) and the organics were extracted with ether (2×200 mL). The extracts were combined and silica gel was added. The solvents were removed and the adsorbate was flash chromatographed (90/10 petroleum ether/ethyl acetate) without achieving purification. The recovered material was purified by high pressure liquid chromatography which gave recovered starting material (30.5%) and gave the title compound as a white solid (0.835 g, 30%): mp 212-213° C.; NMR (DMSO-d6); δ8.09 (d, J=8 Hz, 1H), 7.64-7.58 (m, 1H), 7.54-7.42 (m, 5H), 7.43 (d, J=8 Hz, 1H), 3.47 (s, 3H, SO3CH3), 2.42 (s, 3H), 1.50 (s, 3); MS(EI): [M+] 508 (100%); Anal. calc. for C21H17IO3S2, C, 49.61; H, 3.37; N, 0.00. Found: C, 49.44; H, 3.52; N, 0.03.

Provenance & Evidence