(4-Hydroxy-3,5-diiodo-phenyl)-phenyl-methanone → 4-(4-Benzoyl-2,6-diiodo-phenoxysulfonyl)-2-hydroxy-benzoic acid

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Reaction Steps

The title compound was prepared according to the procedure in Example 4 using (4-hydroxy-3,5-diiodo-phenyl)-phenyl-methanone (0.346 g, 0.768 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.928 g, 3.92 mmol) in THF. Purification On Biotage KP-Sil, eluting with 10% MeOH/CHCl3 followed by crystallization from EtOAc/hexane gave 0.15 g (30%) of the title compound as an orange solid, mp 190° C. 1H NMR (DMSO-d6) δ 7.22-7.35 (m, 2H), 7.58 (t, 2H), 7.69-7.75 (m, 3H), 7.95 (d, 1H), 8.10 (s, 2H). IR (KBr) 3400, 3100, 1660, 1280 and 1180 cm-1. mass spectrum (+FAB) m/z 651 (M+H). Anal. Calcd. for C20H12I2O7S 0.5H2O: C,36.44; H,1.99; N,0.00. Found: C,36.50; H,2.16; N,0.09.

Provenance & Evidence