Iodine → Methanesulfonic acid 4-(6-Iodo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenyl ester

Participants

Reaction Steps

To a solution of methanesulfonic acid 4-benzo[b]naphtho[2,3-d]thiophen-11-yl-phenyl ester (2.24 g, 5.54 mmole) in tetrahydrofuran (22.4 mL), 80% aqueous acetic acid (11.2 mL) and sulfuric acid (0.6 mL) was added iodine (0.984 g, 3.87 mmol) and iodic acid (0.244 g, 1.39 mmol). The reaction mixture was stirred for 88 h at room temperature then combined with an aqueous solution of sodium bisulfite (100 mL). The organics were extracted with ether (500 mL). The extracts were concentrated and chased with benzene and pet ether to provide the title compound as a yellow solid (2.75 g, 94%): mp 176-186° C.; NMR (CDCl3); δ 8.24 (ddd, J=8, 1, 1 Hz, 1H), 7.81 (ddd, J=8, 1, 1 Hz, 1H), 7.65-7.58 (m, 3H), 7.52-7.38 (m, 5H), 7.11-7.07 (ddd, J=8, 7, 1 Hz, 1H), 6.57 (ddd, J=8, 1, 1 Hz, 1H), 3.33 (s, 3H); MS (+FAB): [M+] m/z 530 (65%), [M+H]+m/z 531 (25%); Anal. calc. for C23H15IO3S2: C, 52.08, H, 2.85, N, 0.00. Found: C, 51.75, H, 2.75, N, 0.06.

Provenance & Evidence