Reacción #345005

Ecuación de reacción

sodium hydride

methyl 2-bromophenylacetate

ethyl acetate

2-chloro-4-methylphenol

→

title compound

Rendimiento 83.1%

methyl 2-(2-chloro-4-methylphenoxy)-2-phenylacetate

Rendimiento 83.1%

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGthe reaction was stirred an additional 1.5 hours
3. 3
   Lavadowashed with water
4. 4
   Secadodried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated
7. 7
   OtroThe residue was purified on a silica gel flash chromatography column
8. 8
   Lavadoeluted with 4% ethyl acetate/hexane

Procedimiento

To a suspension of 0.282 g (7.04 mmol) of a 60% oil dispersion of sodium hydride in DMF was added 1.00 g (7.04 mmol) of 2-chloro-4-methylphenol and the mixture was stirred under an N2 atmosphere at room temperature. After 10 minutes, a solution of 1.94 g (8.45 mmol) of methyl 2-bromophenylacetate dissolved in 10 mL of DMF was added and the reaction was stirred an additional 1.5 hours. The reaction was then diluted into ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 4% ethyl acetate/hexane to afford 1.70 g (83%) of the title compound.

Fuente