Iodine → HCID 67512931, compound

Participants

Reaction Steps

Iodine (0.147 mL, 2.85 mmol) and [bis(trifluoroacetoxy)iodo]benzene (1.224 g, 2.85 mmol) were added successively to a solution of methyl 3-(4-methoxyphenyl)isoxazole-5-carboxylate (1.021 g, 4.38 mmol) in CH2Cl2 (13.2 mL) at 25° C. and the reaction was stirred overnight. After this time the solvent was removed in vacuo to give the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 20% EtOAc in hexanes over 2088 mL, gradient to 40% EtOAc in hexanes over 2448 mL) to afford methyl 3-(3-iodo-4-methoxyphenyl)isoxazole-5-carboxylate, as a colorless oil. LCMS calc.=359.97. found=359.81 (M+H)+. 1H NMR (600 MHz, CDCl3): δ 8.24 (d, J=2.1 Hz, 1H); 7.78 (dd, J=8.5, 2.2 Hz, 1H); 7.19 (s, 1H); 6.89 (d, J=8.5 Hz, 1H); 3.99 (s, 3H); 3.93 (s, 3H).

Provenance & Evidence