반응 #2186129

반응 방정식

3-bromophenol

cyclopropyl bromide

sodium iodide

cesium carbonate

→

oil

수율 21.0%

3-Bromophenyl cyclopropyl ether

수율 21.0%

용매

EtOAc

DMF

반응 조건

후처리

1. 1
   온도the reaction was cooled to room temperature
2. 2
   세척washed with water
3. 3
   추출extracted three times with EtOAc
4. 4
   건조The combined organic layers were dried over sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by silica gel flash chromatography (0-5% EtOAc/hexane)

실험 절차

To a solution of 3-bromophenol (0.57 g, 3.29 mmol) (commercially available from Aldrich) in dry DMF (5.0 mL) was added cyclopropyl bromide (0.53 mL, 6.62 mmol) (commercially available from Aldrich), sodium iodide (50.1 mg, 0.334 mmol), and cesium carbonate (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 T24.1 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.).

출처