Reaction #1595

Reaction equation

1,1,2 trichloro-2,3,3-trifluorocyclobutane

H2O

HCl

→

colorless liquid

Yield 79.0%

1,4-dichloro-1,2,2-trifluorocyclobut-3-ene

Yield 79.0%

Solvents

ether

triethylamine

Conditions

Workup

1. 1
   WashThe ether layer was washed with H2O (100 ml), brine (100 ml)
2. 2
   Dryingdried over anhydrous MgSO4
3. 3
   Otherevaporated in vacuo
4. 4
   workup.DISTILLATIONThe residue was distilled fractionally atmospheric pressure from 64°-68° C.

Procedure

To a solution of 1,1,2 trichloro-2,3,3-trifluorocyclobutane (55.5 g) in 100 ml of anhydrous ether, triethylamine (40 ml) was added dropwise over 30 min at room temperature, and the mixture was stirred overnight at ambient temperature. The mixture was then stirred with 120 ml H2O and 7.5 ml of concentrated HCl. The ether layer was washed with H2O (100 ml), brine (100 ml), dried over anhydrous MgSO4, and evaporated in vacuo. The residue was distilled fractionally atmospheric pressure from 64°-68° C. to yield 36 g (79%) of a colorless liquid as pure product.

Source