Magnesium → 5-Cyclopropyl-1,3-benzodioxole

HRID 963839Notes

Reaction equation

HRID 963839 reaction equation
FC1C=CC(Br)=CC=1[O:9]C1C=CC=CC=1.[Mg].C(OCC(F)=C[C:24]1([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH:34](F)F)=[CH:29][CH:28]=2)[CH2:26][CH2:25]1)(=O)C>O1CCCC1>[CH2:34]1[O:33][C:30]2[CH:29]=[CH:28][C:27]([CH:24]3[CH2:25][CH2:26]3)=[CH:32][C:31]=2[O:9]1

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 11076399Benzene, 4-bromo-1-fluoro-2-phenoxy-HCID 544373871-(3-Acetoxy-2-fluoroprop-1-enyl)-1-(4-difluoromethoxyphenyl)cyclopropane

Product 1

HCID 162050505-Cyclopropyl-1,3-benzodioxoleYield 143.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 25 was repeated using a Grignard reagent, prepared from 4-fluoro-3-phenoxyphenyl bromide (0.31 g), tetrahydrofuran (2 ml) and magnesium (20 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(4-difluoro-methoxyphenyl)cyclopropane (Example 24) (0.155 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C18; solvent: methanol; flow rate: 8 ml/min) to afford 1-(4-difluoromethoxyphenyl)-3-(4-fluoro-3-phenoxyphenyl)prop-1-enyl)-1-(3,4-methylenedioxyphenyl)cyclopropane (120 mg, 54%).

Workup

  1. customThe residue after evaporation
  2. customwas purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9)

Sources & evidence

ORD record
ord-18d126dcb0e841bfa5ebfca8bff057e1
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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