Reacción #1973980

Ecuación de reacción

methyl bromo-acetate

1-(4-bromo-2-hydroxyphenyl)ethanone

sodium hydride

→

title compound

Rendimiento 82.0%

methyl 2-(2-acetyl-5-bromophenoxy)acetate

Rendimiento 82.0%

Disolventes

ethyl acetate

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGby stirring at room temperature for 18 h
2. 2
   Extracciónextracted with water (4×) and saturated sodium chloride solution
3. 3
   OtroDrying
4. 4
   Concentración(Na2SO4) and concentration in vacuo
5. 5
   Otroafforded a nearly colorless solid, which
6. 6
   Otrowas purified by column chromatography on silica gel
7. 7
   Lavadoeluting with 20-100% ethyl acetate in hexanes

Procedimiento

A solution of 1-(4-bromo-2-hydroxyphenyl)ethanone (1.35 g, 6.28 mmol) in anhydrous DMF (16 mL) was treated in several portions with sodium hydride (377 mg of 60% in oil, 226 mg, 9.42 mmol) followed by stirring at room temperature for 30 min. The mixture was then treated with methyl bromo-acetate (871 μL, 1.45 g, 9.48 mmol) dropwise (solution became warm after addition was complete) followed by stirring at room temperature for 18 h. The mixture was diluted with ethyl acetate and extracted with water (4×) and saturated sodium chloride solution. Drying (Na2SO4) and concentration in vacuo afforded a nearly colorless solid, which was purified by column chromatography on silica gel, eluting with 20-100% ethyl acetate in hexanes. These procedures afforded the title compound as a colorless solid (1.47 g, 82%).

Fuente