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

HRID 963804Notes

Reaction equation

HRID 963804 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:11]=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(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:11][C:8]1([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10]1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 13612258Methyl 2,2-dichloro-2-fluoroacetateHCID 232981831-(4-Fluorophenyl)cyclopropanecarbaldehyde

Product 1

HCID 538164181-(2-Fluoro-2-(methoxycarbonyl)ethenyl)-1-(4-fluorophenyl)cyclopropaneYield 42%

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) and molecular sieve 4A (1 g), tetrahydrofuran (18 ml), 1-(4-fluorophenyl)-1-formyl-cyclopropane (0.54 g), acetic anhydride (0.38 ml) and methyl dichlorofluoroacetate (0.69 g) to yield the title compound (0.32 g, 42%).

Sources & evidence

ORD record
ord-89d040376aff4d51a3c4c583fe2fc9f0
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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