Reacción #2186129

Ecuación de reacción

3-bromophenol

cyclopropyl bromide

sodium iodide

cesium carbonate

→

oil

Rendimiento 21.0%

3-Bromophenyl cyclopropyl ether

Rendimiento 21.0%

Disolventes

EtOAc

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction was cooled to room temperature
2. 2
   Lavadowashed with water
3. 3
   Extracciónextracted three times with EtOAc
4. 4
   SecadoThe combined organic layers were dried over sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was purified by silica gel flash chromatography (0-5% EtOAc/hexane)

Procedimiento

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.).

Fuente