Реакция #79939

Уравнение реакции

ethyl acetate

3,3,-dimethyl acryloyl chloride

sodium hydride

4-bromo phenol

→

title compound

Выход 59.0%

3-Methyl-but-2-enoic acid 4-bromo-phenyl ester

Выход 59.0%

Растворители

brine

hexane

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ТемператураTo a stirred, cooled
2. 2
   workup.ADDITIONwas added
3. 3
   Экстракцияextracted with diethyl ether (×2)
4. 4
   СушкаThe combined organic phase was dried over anhydrous sodium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Другоеevaporated in vacuo
7. 7
   Другоеto afford an oil which

Методика

To a stirred, cooled (ice bath) suspension of sodium hydride (2.4 g, 100 mmol) in anhydrous tetrahydrofuran (200 mL), 4-bromo phenol (17.3 g, 100 mmol) was added followed by 3,3,-dimethyl acryloyl chloride (11.14 mL, 100 mmol). After 4 hours at ambient temperature, the reaction mixture was poured into brine and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 2% ethyl acetate in hexane as the eluent to afford the title compound (15 g, 59%).

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