(1-Acetoxy-2,2-dichloro-3,3,3-trifluoropropyl)-2,3-dichlorobenzene → (2-Chloro-3,3,3-trifluoropropen-1-yl)-2,3-dichlorobenzene

HRID 1607909Notes

Reaction equation

C(O[CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[Cl:20])[C:6](Cl)([Cl:11])[C:7]([F:10])([F:9])[F:8])(=O)C>C(O)(=O)C.[Zn]>[Cl:11][C:6]([C:7]([F:8])([F:9])[F:10])=[CH:5][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[Cl:20]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 59.0 g of (1-acetoxy-2,2-dichloro-3,3,3-trifluoropropyl)-2,3-dichlorobenzene in 350 ml of acetic acid is heated to 40° C., and 13.0 g of zinc powder are added portionwise. To effect completion of the reaction, the reaction mixture is heated at 90° C. for 3 hours. In further processing, thereaction mixture is taken up in ice-water, and extracted with ether. The combined organic phases are washed with water, sodium hydrogen carbonate solution and sodium chloride solution; they are then dried over magnesium sulfate, and concentrated by evaporation to thus obtain (2-chloro-3,3,3-trifluoropropen-1-yl)-2,3-dichlorobenzene in the form of yellow oil (compound No. 4.10).

Workup

customcompletion of the reaction
extractionextracted with ether
washThe combined organic phases are washed with water, sodium hydrogen carbonate solution and sodium chloride solution
dry with materialthey are then dried over magnesium sulfate
concentrationconcentrated by evaporation to thus obtain (2-chloro-3,3,3-trifluoropropen-1-yl)-2,3-dichlorobenzene in the form of yellow oil (compound No

Sources & evidence

ORD record: ord-4212126600c34534939c0881d70c3edf
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04868202

Reaction notes

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