Reaction #215701

Reaction equation

2-bromo-3,4,5,6-tetrafluorobenzoyl chloride

magnesium chloride

diethyl malonate

hydrochloric acid

triethylamine

→

Diethyl (2-bromo-3,4,5,6-tetrafluoro-benzoyl)malonate

Solvents

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONare added dropwise
2. 2
   Temperaturewhile cooling
3. 3
   workup.STIRRINGthe mixture is subsequently stirred at 0° C. for a further hour
4. 4
   workup.WAITbrought to room temperature overnight
5. 5
   Extractionthe mixture is extracted three times with methylene chloride
6. 6
   Dryingthe extract is dried with Na2SO4
7. 7
   Concentrationconcentrated in vacuo

Procedure

15.9 g (0.167 mol) of magnesium chloride in 150 ml of anhydrous acetonitrile (dried over zeolite) are initially introduced into the reaction vessel and 26.9 g (0.167 mol) of diethyl malonate are added dropwise, while cooling. The mixture is cooled to 0° C., 46 ml (33.7 g=0.33 mol) of triethylamine are added dropwise and the mixture is subsequently stirred for 30 minutes. 48.9 g (0.168 mol) of 2-bromo-3,4,5,6-tetrafluorobenzoyl chloride are then added dropwise and the mixture is subsequently stirred at 0° C. for a further hour and brought to room temperature overnight. 100 ml of 5N hydrochloric acid are added, the mixture is extracted three times with methylene chloride and the extract is dried with Na2SO4 and concentrated in vacuo.

Source