Bis(trifluoroacetoxy)iodobenzene → 4-[[3-Methyl-4-(4-trifluoromethylbenzyloxy)phenyl]sulfanyl]-2-propylphenoxy-acetic acid ethyl ester

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Reaction Steps

Compound 4.4 (5.0 g, 19.66 mmol) was dissolved in 1,1,1,3,3,3-hexafluoro-2-propanol (30 mL) under argon atmosphere. To the solution was added compound 4.1 (5.23 g, 19.66 mmol) and [bis(trifluoroacetoxy)iodo]benzene (10.14 g, 23.59 mmol) slowly, while maintaining the reaction temperature between 10° C. and 17° C. After stirring for 15 min, the reaction mixture was concentrated in vacuo to give a residue which was purified using silica gel column chromatography (hexane/EtOAc=20/1) to give 4.5 (6.11 g). 1H NMR (400 MHz) (CDCl3) δ 7.64 (2H, d, J=8.2 Hz); 7.54 (2H, d, J=8.1 Hz); 7.20-7.06 (4H, m); 6.76 (1H, d, J=8.4 Hz); 6.62 (1H, d, J=8.4 Hz); 5.11 (2H, s); 4.60 (2H, s); 4.25 (2H, q, J=7.1 Hz); 2.63-2.56 (2H, m); 2.24 (3H, s); 1.67-1.55 (2H, m); 1.28 (3H, t, J=7.1 Hz); 0.92 (3H, t, J=7.4 Hz).

Provenance & Evidence