Reaction #1435737

Reaction equation

tert-butyl methyl ether

sodium hydride

ethyl malonate

1-bromo-2,6-difluorobenzene

hydrochloric acid

→

diethyl (2,6-difluorophenyl)malonate

Solvents

water

1,4-dioxane

Conditions

Workup

1. 1
   workup.ADDITIONwere added dropwise at 60° C.
2. 2
   Temperaturerefluxed for 16 hours
3. 3
   Temperatureunder heating
4. 4
   Temperaturecooling
5. 5
   WashThe separated organic layer was washed with dil. hydrochloric acid and water subsequently
6. 6
   Dryingdried over sodium sulfate
7. 7
   Concentrationconcentrated
8. 8
   workup.DISTILLATIONThe residue was distilled under reduced pressure

Procedure

Into a mixture of 8.00 g of sodium hydride (60% in oil) and 100 ml of 1,4-dioxane, 32.0 g of ethyl malonate were added dropwise at 60° C. , further 14.6 g of cuprous bromide and 19.3 g of 1-bromo-2,6-difluorobenzene were added subsequently, and then refluxed for 16 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 separated organic layer was washed with dil. hydrochloric acid and water subsequently, dried over sodium sulfate and concentrated. The residue was distilled under reduced pressure to give 16.5 g of diethyl (2,6-difluorophenyl)malonate. b.p. 107–109° C. (0.14 mmHg)

Source