反応 #1973980

反応方程式

methyl bromo-acetate

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

sodium hydride

→

title compound

収率 82.0%

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

収率 82.0%

溶媒

ethyl acetate

DMF

反応条件

後処理

1. 1
   workup.STIRRINGby stirring at room temperature for 18 h
2. 2
   抽出extracted with water (4×) and saturated sodium chloride solution
3. 3
   その他Drying
4. 4
   濃縮(Na2SO4) and concentration in vacuo
5. 5
   その他afforded a nearly colorless solid, which
6. 6
   その他was purified by column chromatography on silica gel
7. 7
   洗浄eluting with 20-100% ethyl acetate in hexanes

実験手順

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%).

出典