Acetic Anhydride → 1-(2-Fluoro-2-(methoxycarbonyl)ethenyl)-1-(4-trifluoromethoxyphenyl)cyclopropane

HRID 963803Notes

Reaction equation

HRID 963803 reaction equation
[CH:1]([C:3]1([C:6]2[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=2)[CH2:5][CH2:4]1)=O.C(OC(=O)C)(=O)C.Cl[C:25](Cl)([F:30])[C:26]([O:28][CH3:29])=[O:27]>[Zn].[Cu]Cl.O1CCCC1>[F:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:1][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=2)[CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 13612258Methyl 2,2-dichloro-2-fluoroacetateHCID 190833401-[4-(Trifluoromethoxy)phenyl]cyclopropane-1-carbaldehyde

Product 1

HCID 544656881-(2-Fluoro-2-(methoxycarbonyl)ethenyl)-1-(4-trifluoromethoxyphenyl)cyclopropaneYield 34%

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 (0.16 g), molecular sieve 4A (1.1 g), tetrahydrofuran (18 ml), 1-formyl-1-(4-trifluoromethoxyphenyl)cyclopropane (1.08 g), acetic anhydride (0.6 ml) and methyl dichlorofluoroacetate (0.86 g) to yield the title compound (0.45 g, 34%).

Sources & evidence

ORD record
ord-2cf218033db34ecfaa9fb068f016453b
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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