Réaction #44760

Équation de réaction

water

4-(benzyl)phenol

1-bromo-2-chloroethane

cesium carbonate

→

1-(2-chloroethoxy)-4-(benzyl)benzene

Rendement 86.0%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 12 hours
2. 2
   TempératureAfter cooling
3. 3
   ExtractionThe mixture was extracted with ethyl acetate
4. 4
   LavageThe organic layer was washed with brine
5. 5
   Séchagedried over sodium sulfate
6. 6
   Concentrationconcentrated under reduced pressure

Mode opératoire

A solution of 4-(benzyl)phenol (638 mg, 3.46 mmol), 1-bromo-2-chloroethane (2.3 mL, 27.7 mmol) and cesium carbonate (4.5 g, 27.7 mmol) in 35 mL of acetonitrile was heated at reflux for 12 hours. After cooling, water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Flash chromatography gave 734 mg of 1-(2-chloroethoxy)-4-(benzyl)benzene, 1H NMR (300 MHz, CDCl3) δ 7.29 (dd, 2H), 7.19 (dd, 1H), 7.18 (d, 2H), 7.12 (d, 2H), 6.85 (d, 2H), 4.21 (t, 2H), 3.93 (s, 2H), 3.80 (t, 2H) ppm.

Source