Magnesium → 1-(2-Fluoro-3-(4-fluoro-3-phenoxy-phenyl)prop-1-enyl)-1-(4-fluorophenyl)cyclopropane

HRID 963835Notes

Reaction equation

HRID 963835 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Mg].C(O[CH2:21][C:22]([F:34])=[CH:23][C:24]1([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:26][CH2:25]1)(=O)C>O1CCCC1>[F:34][C:22]([CH2:21][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=1)=[CH:23][C:24]1([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 11076399Benzene, 4-bromo-1-fluoro-2-phenoxy-HCID 536458661-(3-Acetoxy-2-fluoroprop-1-enyl)-1-(4-fluorophenyl)cyclopropane

Product 1

HCID 190833521-(2-Fluoro-3-(4-fluoro-3-phenoxy-phenyl)prop-1-enyl)-1-(4-fluorophenyl)cyclopropaneYield 37%

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 (0.3 g), tetrahydrofuran (2 ml) and magnesium (21 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(4-fluorophenyl)-cyclopropane (Example 20) (88 mg). 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: 2 ml/min) to afford 1-(2-fluoro-3-(4-fluoro-3-phenoxy-phenyl)prop-1-enyl)-1-(4-fluorophenyl)cyclopropane (45.6 mg, 37%).

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-19b61c4852ea4f41b8253948c47b8aa1
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

Loading…