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

HRID 963808Notes

Reaction equation

HRID 963808 reaction equation
[F:1][CH:2]([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH:13]=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C(OC(=O)C)(=O)C.Cl[C:24](Cl)([F:29])[C:25]([O:27][CH3:28])=[O:26]>[Zn].[Cu]Cl.O1CCCC1>[F:1][CH:2]([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH:13]=[C:24]([F:29])[C:25]([O:27][CH3:28])=[O:26])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 13612258Methyl 2,2-dichloro-2-fluoroacetateHCID 190833421-[4-(Difluoromethoxy)phenyl]cyclopropane-1-carbaldehyde

Product 1

HCID 539014161-(4-Difluoromethoxyphenyl)-1-(2-fluoro-2(methoxycarbonyl)ethenyl)cyclopropaneYield 28%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 1 was repeated using zinc powder (2.8 g), copper (I) chloride (0.42 g), molecular sieve 4A (2.8 g) tetrahydrofuran (50 ml), 1-(4-difluoromethoxyphenyl)-1-formylcyclopropane, acetic anhydride (1.5 ml) and methyl dichlorofluoroacetate (3.6 g) to yield the title compound (0.79 g, 28%).

Sources & evidence

ORD record
ord-7182948a159947419d437f1f4683d20d
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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