反应详情

温度

150 °C

To a solution of 3-bromophenol (0.57 g, 3.29 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) in dry DMF (5.0 mL) was added cyclopropyl bromide (0.53 mL, 6.62 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), sodium iodide (50.1 mg, 0.334 mmol), and Cs2CO3 (3.2 g, 9.86 mmol). The reaction mixture was heated in a pressure tube to 150° C. After 19 hours, the reaction was cooled to room temperature then diluted with EtOAc, washed with water, and extracted three times with EtOAc. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel flash chromatography (0-5% EtOAc/hexane) to afford T32.1 as a colorless oil (144 mg, 21% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.29 (1H, m), 7.19 (2H, m), 6.99 (1H, d, J=7.8 Hz), 3.74 (1H, ddd, J=8.9, 5.8, 3.3 Hz), 0.81 (4H, ddd, J=11.2, 9.0, 8.8 Hz.).

1. temperaturethe reaction was cooled to room temperature
2. washwashed with water
3. extractionextracted three times with EtOAc
4. dry with materialThe combined organic layers were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by silica gel flash chromatography (0-5% EtOAc/hexane)