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

Participants

Reaction Conditions

Reaction Steps

A suspension of methanesulfonic acid 4-(6-iodo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenyl ester (1.65 g, 3.11 mmole), tetramethyltin (3.58, 25.8 mmole), and bis(triphenylphosphine)palladium II chloride (0.218 g, 0.311 mmole 10 mole %) in dry N,N dimethylformamide (16 mL) was heated in a sealed vessel under argon at 103° C. for 4 hours and left at room temperature overnight. The reaction mixture was added to water (200 mL) and extracted with ether. Silica gel (40 mL) was added and the solvent removed. The adsorbate was flash chromatographed (85:15 Petroleum ether:ethyl acetate) to give the title compound as a pale yellow solid (1.12 g, 86%): mp 172-173° C.; NMR (CDCl3); δ 8.18 (ddd, J=8, 1, 1 Hz, 1H), 7.81 (ddd, J=1, 1, 8 Hz, 1H), 7.62-7.55 (m, 3H), 7.50-7.48 (m, 2H), 7.44-7.34 (m, 2H), 7.06 (ddd, J=8, 7, 1 Hz, 1H), 6.64 (ddd, J=8, 1, 1 Hz), 3.32 (s, 3H), 2.99 (s, 3H); MS: EI [m/z] 418 (100%); Anal. Calcd. for C24H18O3S2: C, 68.87, H, 4.34, N, 0.00. Found: C, 68.60, H, 4.26, N, 0.02.

Provenance & Evidence