Lithium iodide → HCID 54224375, compound

Participants

Reaction Steps

A solution of (R)-2-[2,6-dibromo-4-(2-bromo-dibenzothiophen-1-yl)-phenoxy]-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyric acid methyl ester (0.514 g, 0.68 mmol) and lithium iodide (0.915 g, 6.8 mmol) in pyridine (20 mL) was stirred at 110° C. After 2 days, the mixture was quenched with 10% aqueous HCl and further diluted with water (150 mL). Aqueous mixture was extracted with dichloromethane (150 mL). The dichloromethane extract was washed with water, dried with brine. Silica gel was added. Solvent was removed and the adsorbate was flash chromatographed (eluent 7:3 petroleum ether:ethyl acetate) to provide the title compound as a white solid (0.319 g, 63%): mp 130-132° C.: NMR (CDCl3): δ 7.86 (dd, J=8, 1 Hz, 2H), 7.81 (d, J=8 Hz, 1H), 7.77-7.70 (m, 4 H), 7.52 (d, J=1 Hz, 2H), 7.39 (ddd, J=8, 7, 1 Hz, 1H), 7.18 (ddd, J=8, 7, 1 Hz, 1H), 6.77 (d, J=8 Hz, 1H), 5.24 (t, J=7 Hz, 1H), 4.21-4.05 (m, 2 H), 2.67-2.55 (m, 2H); MS (+EI): [M+], 3 bromine isotope pattern, 741, 743, 745, 747; Anal. Calc. for C3OH18Br3NO5S: C 48.86, H, 2.74, N, 1.83. Found: C 48.90, H, 2.82, N, 1.18.

Provenance & Evidence