Iodine → 2-(4-Bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole

関与物質

反応条件

反応手順

Add iodine (1.90 g, 7.49 mmol) to a stirred mixture of 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol (1.503 g, 5.33 mmol), triphenylphosphine (2.101 g, 8.01 mmol), and pyridine (1.4 mL, 17 mmol) in toluene (48 mL) and heat at 100° C. for 45 min. Cool to room temperature, add ethyl acetate and water, and separate the layers. Extract the aqueous layer twice with ethyl acetate, wash the organic layer with 0.1N HCl, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure. Purify the residue by flash chromatography (SiO2, elute 0% to 10% EtOAc/hexanes) to-yield 1.804 g of the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 7.89 (d, J=8.4 Hz, 2H), 7.60 (d, J=8.8 Hz, 2H), 3.49 (dd, J=7.2, 7.2 Hz, 2H), 3.11 (dd, J=7.2, 7.2 Hz, 2H), 2.39 (s, 3H).

情報源と証拠