Reacción #91550

Ecuación de reacción

DEAD

(4-chloro-2-pyridinyl)methanol

1-(3-bromo-4-hydroxyphenyl)ethanone

triphenylphosphine

→

title compound

1-(3-bromo-4-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)ethanone

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturabefore cooling
2. 2
   workup.STIRRINGThis was stirred for 16 h
3. 3
   OtroThe reaction mixture was partitioned between water and ethyl acetate
4. 4
   Lavadothe combined organics were washed with brine
5. 5
   Secadodried over sodium sulfate
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThis was purified through silica eluting with 0-35% ethyl acetate in hexane

Procedimiento

To a stirred solution of (4-chloro-2-pyridinyl)methanol (Commercial eg Aldrich) (0.2 g) in THF (5 ml) were added 1-(3-bromo-4-hydroxyphenyl)ethanone (0.3 g) and triphenylphosphine (0.547 g). This was stirred for 10 min before cooling and adding slowly DEAD (0.363 g). This was stirred for 16 h. The reaction mixture was partitioned between water and ethyl acetate. The aqueous was reextracted with ethyl acetate and the combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. This was purified through silica eluting with 0-35% ethyl acetate in hexane to give the title compound, 0.30 g

Fuente