Reaction #76175

Reaction equation

cyclopropylamine

ethyl 2,4,6-trichloro-3,5-difluorobenzoylacetate

triethyl orthoformate

diacetyl oxide

→

ethyl 2-(2,4,6-trichloro-3,5-difluorobenzoyl)-3-cyclopropylaminoacrylate

Yield 74.8%

Conditions

Workup

1. 1
   Otherwere evaporated under reduced pressure
2. 2
   workup.ADDITIONTo the residue was added 250 ml of anhydrous ethanol
3. 3
   FiltrationThe resultant mixture was filtered under suction
4. 4
   OtherThe residue was re-crystallized from a mixture of petroleum ether and cyclohexane

Procedure

82.9 g of ethyl 2,4,6-trichloro-3,5-difluorobenzoylacetate (0.25 mol), 66.6 g of triethyl orthoformate (0.45 mol) and 77.4 g of diacetyl oxide (0.72 mol) were stirred at 150° C. for 2.5 hours. Fractions having a lower boiling point were evaporated under reduced pressure. To the residue was added 250 ml of anhydrous ethanol. 14.5 g of cyclopropylamine (0.25 mol) was added to the solution under cooling of ice water and the reaction was then carried at room temperature for 2 hours. The resultant mixture was filtered under suction. The residue was re-crystallized from a mixture of petroleum ether and cyclohexane to yield 74.5 g (0.187 mol) of ethyl 2-(2,4,6-trichloro-3,5-difluorobenzoyl)-3-cyclopropylaminoacrylate in 74.6% yield.

Source