Реакция #1973980

Уравнение реакции

methyl bromo-acetate

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

sodium hydride

→

title compound

Выход 82.0%

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

Выход 82.0%

Растворители

ethyl acetate

DMF

Условия реакции

Обработка

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

Методика

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%).

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