反応 #1435724

反応方程式

hydrochloric acid

sodium hydride

diethyl malonate

1-bromo-2,4,6-trifluorobenzene

→

diethyl (2,4,6-trifluorophenyl)malonate

収率 43.4%

溶媒

1,4-dioxane

water

tert-butyl methyl ether

反応条件

後処理

1. 1
   workup.ADDITIONwere added dropwise at room temperature
2. 2
   温度under heating
3. 3
   温度cooling
4. 4
   その他The organic layer was separated
5. 5
   洗浄washed with aqueous sodium hydroxide solution, dil. hydrochloric acid and water subsequently
6. 6
   乾燥dried over sodium sulfate
7. 7
   濃縮concentrated

実験手順

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.

出典