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

HRID 963805Notes

Reaction equation

HRID 963805 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1([CH:15]=O)[CH2:14][CH2:13]1.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:15][C:12]1([C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=2[F:1])[CH2:13][CH2:14]1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 13612258Methyl 2,2-dichloro-2-fluoroacetateHCID 190833351-[2-Fluoro-4-(trifluoromethyl)phenyl]cyclopropane-1-carbaldehyde

Product 1

HCID 541601341-(2-Fluoro-2-(methoxycarbonyl)ethenyl)-1-(2-fluoro-4-trifluoromethylphenyl) cyclopropaneYield 44%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 1 was repeated using zinc powder (1.3 g), copper (I) chloride (0.22 g), molecular sieve 4A (1.6 g), tetrahydrofuran (20 ml), 1-(2-fluoro-4-tri-fluoromethylphenyl)-1-formylcyclopropane (1.39 g), acetic anhydride (0.58 ml) and methyl dichlorofluoroacetate to yield the title compound (0.81 g, 44%).

Sources & evidence

ORD record
ord-d3f6d3674a45445c9403249d4357c0f8
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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