Reaction Steps
To a solution of 3-(furan-2-yl)-4-phenyl-5-methylisoxazole (0.152 g, 0.670 mmol) in anhydrous DMF (6 ml), kept stirring at 0° C., is slowly added NBS (0.144 g, 0.810 mmol). A suspension is formed which is kept stirring for 2 h at ambient temperature. Water is then added, and then ethyl acetate. The two phases are separated and the aqueous phase is extracted three times with ethyl acetate. The total organic phase is first washed with a saline aqueous solution (NaCl) and then dried with anhydrous Na2SO4. The solvent is evaporated at reduced pressure. A yellow solid is obtained. When subjected to chromatography (silica gel, petroleum ether/ethyl acetate=9:1) it gave the product with 60% yield, as a white solid; m.p. 93-96° C. (hexane). FT-IR (KBr): 3143, 3055, 2962, 2923, 2851, 1632, 1605, 1505, 1434, 1408, 1236, 1202, 1122, 1019, 984, 921, 896, 796, 774, 721, 704, 676, 561 cm−1. 1H NMR (400 MHz, CDCl3, δ): 7.44-7.35 (m, 3H, aromatic protons); 7.26-7.23 (m, 2H, aromatic protons); 6.24 (d, 1H, J=3.3 Hz, furyl proton); 6.20 (d, 1H, J=3.3 Hz, furyl proton); 2.34 (s, 3H). 13C NMR (100 MHz, CDCl3, δ): 166.7, 152.1, 145.8, 129.9, 129.3, 128.7, 128.3, 124.1, 114.6, 113.8, 112.9, 11.1. GC-MS (70 eV) m/z (rel.int.): 305 [(M++2), 47], 303 (M+, 100), 264 (13), 263 (98), 262 (23), 261 (100), 234 (10), 232 (10), 154 (54), 153 (33), 129 (12), 127 (31), 77 (9), 43 (14). Anal. Calc. For C14H10BrNO2: C, 55.29; H, 3.31; N, 4.61. Found: C, 55.08; H, 3.60; N, 4.20.
