Acetic Anhydride → 1-(2,4-Difluorophenyl)-1-(2-fluoro-2(methoxycarbonyl)ethenyl)cyclopropane

HRID 963807Notes

Reaction equation

HRID 963807 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH:12]=O)[CH2:11][CH2:10]1.C(OC(=O)C)(=O)C.Cl[C:22](Cl)([F:27])[C:23]([O:25][CH3:26])=[O:24]>[Zn].[Cu]Cl.O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH:12]=[C:22]([F:27])[C:23]([O:25][CH3:26])=[O:24])[CH2:10][CH2:11]1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 13612258Methyl 2,2-dichloro-2-fluoroacetateHCID 190833661-(2,4-Difluorophenyl)cyclopropane-1-carbaldehyde

Product 1

HCID 543230221-(2,4-Difluorophenyl)-1-(2-fluoro-2(methoxycarbonyl)ethenyl)cyclopropaneYield 39%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 1 was repeated using zinc powder (1 g), copper (I) chloride (0.12 g), molecular sieve 4A (1 g), tetrahydrofuran (18 ml), 1-(2,4-difluorophenyl)-1-formylcyclopropane (0.44 g), acetic anhydride (0.4 ml) and methyl dichlorofluoroacetate (0.62 g) to yield the title compound (0.24 g, 39%).

Sources & evidence

ORD record
ord-22d797702f0c4b52991988f90c94314b
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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