Реакция #1435724

Уравнение реакции

hydrochloric acid

sodium hydride

diethyl malonate

1-bromo-2,4,6-trifluorobenzene

→

diethyl (2,4,6-trifluorophenyl)malonate

Выход 43.4%

Растворители

1,4-dioxane

water

tert-butyl methyl ether

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added dropwise at room temperature
2. 2
   Температураunder heating
3. 3
   Температураcooling
4. 4
   ДругоеThe organic layer was separated
5. 5
   Промывкаwashed with aqueous sodium hydroxide solution, dil. hydrochloric acid and water subsequently
6. 6
   Сушкаdried over sodium sulfate
7. 7
   Концентрированиеconcentrated

Методика

Into a mixture of 4.8 g of sodium hydride (60% in oil) and 100 ml of 1,4-dioxane, 19.2 g of diethyl malonate were added dropwise at room temperature, and then 17.2 g of cuprous bromide and 21.1 g of 1-bromo-2,4,6-trifluorobenzene were subsequently added thereto at 40° C. and refluxed for 26 hours under heating. To the reaction mixture, conc. hydrochloric acid was added under ice-cooling, and then tert-butyl methyl ether and water were added. The organic layer was separated, washed with aqueous sodium hydroxide solution, dil. hydrochloric acid and water subsequently, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 12.6 g of diethyl (2,4,6-trifluorophenyl)malonate.

Источник