Acetic Anhydride → 1-(2-Fluoro-2-(methoxycarbonyl)ethenyl)-1-(3,4-methylenedioxyphenyl)cyclopropane

HRID 963806Notes

Reaction equation

HRID 963806 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[CH2:12][CH2:11]3)=[CH:4][C:3]=2[O:2]1.[C:13](OC(=O)C)(=O)C.Cl[C:21](Cl)([F:26])[C:22]([O:24][CH3:25])=[O:23]>[Zn].[Cu]Cl.O1CCCC1>[F:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:13][C:10]1([C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)[CH2:12][CH2:11]1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 13612258Methyl 2,2-dichloro-2-fluoroacetateHCID 162050505-Cyclopropyl-1,3-benzodioxole

Product 1

HCID 538090221-(2-Fluoro-2-(methoxycarbonyl)ethenyl)-1-(3,4-methylenedioxyphenyl)cyclopropaneYield 51%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 1 was repeated using zinc powder (2.94 g), copper (I) chloride (0.45 g) molecular sieve 4A (3 g), tetrahydrofuran (54 ml), 1-formyl-1-(3,4-methylenedioxyphenylcyclopropane (3.09 g), acetic anhydride (1.5 ml) and methyl dichlorofluoroacetate (2.36 g) to yield the title compound (2.2 g, 51%).

Sources & evidence

ORD record
ord-26e31d36616544a6a4f400ba8636a8e6
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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