Reacción #79355

Ecuación de reacción

4-benzyloxyphenol

cesium carbonate

2,2,2-trifluoroethyl trifluoromethanesulfonate

→

benzyl 4-(2,2,2-trifluoroethoxy)phenyl ether

Rendimiento 106.1%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaupon cooling in an ice-water bath
2. 2
   OtroThe cooling bath was removed
3. 3
   workup.ADDITIONThe reaction mixture was diluted with AcOEt and water
4. 4
   OtroThe organic layer was separated
5. 5
   Lavadowashed with 1N hydrochloric acid
6. 6
   Secadodried over anhydrous Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

To a 20 ml DMF solution of 4-benzyloxyphenol (3.35 g, 16.7 mmol) and cesium carbonate (6.02 g, 18.5 mmol) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (4.29 g, 18.4 mmol) upon cooling in an ice-water bath. The cooling bath was removed and the reaction mixture was heated to 50° C. for 1 hr. The reaction mixture was diluted with AcOEt and water. The organic layer was separated, washed with 1N hydrochloric acid, dried over anhydrous Na2SO4, filtered, and concentrated to give benzyl 4-(2,2,2-trifluoroethoxy)phenyl ether 5.0 g (quant.). This material was dissolved in 200 ml of ethanol and was hydrogenated in a Parr shaker with 10% Pd/C 222 mg under hydrogen atmosphere (50 psi) overnight. The catalyst was removed by suction filtration through a pad of celite. The filtrate was concentrated to give the title compound 2.6 g (87%).

Fuente