反应详情

温度

100 °C

To a mixture of 8-chloro-7-hydroxy-1-naphthonitrile (0.127 g, 0.63 mmol) and glacial acetic acid (1 mL) in a pressure tube was added a solution of bromine (0.24 g, 1.5 mmol) in glacial acetic acid (2 mL). The tube was sealed and the mixture was stirred at 100° C. overnight. The reaction was cooled, poured into water (50 mL), and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with sodium bicarbonate solution, dried over sodium sulfate, filtered, stripped of solvent, and purified on a silica column (20% ethyl acetate-hexanes) to yield 0.10 g (56%) of the title compound as a yellow solid. An. analytical sample was prepared by preparative reverse phase HPLC to yield the title compound as a white solid: mp 148–150° C.; 1H NMR (DMSO-d6): δ 7.47 (1H, d, J=8.98 Hz), 7.95 (1H, d, J=9.02 Hz), 8.32 (1H, d, J=2.08 Hz), 8.55 (1H, d, J=2.08 Hz), 11.33 (1H, s); MS (ESI) m/z 280/282/284 (M−H)−.

1. customThe tube was sealed
2. temperatureThe reaction was cooled
3. extractionextracted with ethyl acetate (3×100 mL)
4. washThe combined organic layers were washed with sodium bicarbonate solution
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. custompurified on a silica column (20% ethyl acetate-hexanes)