Water → Methanesulfonic acid 4-Benzo[b]naphtho[2,3-d]thiophen-11-yl-phenyl Ester

Participants

Reaction Steps

Methylsulfonyl chloride (0.63 mL, 8.14 mmol) was added dropwise to a cold (ice bath) solution of 4-benzo[b]naphtho[2,3-d]thiophen-11-yl-phenol (2.00 g, 5.43 mmol) in dry methylene chloride (10 mL) and pyridine (2.08 mL). After stiring at ambient temperature for ca. 36 h. the reaction mixture was combined with water (100 mL). The organics were extracted with ether (100 mL), washed with 10% HCl (100 mL) and concentrated to give the title compound as a white solid (2.51 g, 100%); mp 136-139° C.; NMR (CDCl3); δ 8.38 (s, 1H), 7.97-7.95 (m, 1H), 7.80-7.78 (m, 1H), 7.60-7.50 (m, 6H), 7.43-7.35 (m, 2H), 7.07 (ddd, J=8, 7, 1 Hz, 1H), 6.68 (d, J=8 Hz, 1H), 3.33 (s, 3H); MS (EI): [M+] 404 (100%); Anal. calc. for C23H16O3S2+0.07 C6H14, C, 68.52, H, 4.17, N, 0.03. Found: C, 67.91, H, 3.85, N, 0.06.

Provenance & Evidence