Magnesium → 1-(4-Ethoxyphenyl)-1-(2-fluoro-3-(4-fluoro-3-phenoxyphenyl)-prop-1-enyl)cyclopropane

HRID 963834Notes

Reaction equation

HRID 963834 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:36])=[CH:23][C:24]1([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH3:35])=[CH:29][CH:28]=2)[CH2:26][CH2:25]1)(=O)C>O1CCCC1>[CH2:34]([O:33][C:30]1[CH:31]=[CH:32][C:27]([C:24]2([CH:23]=[C:22]([F:36])[CH2:21][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH:4]=3)[CH2:25][CH2:26]2)=[CH:28][CH:29]=1)[CH3:35]

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 11076399Benzene, 4-bromo-1-fluoro-2-phenoxy-HCID 543885951-(3-Acetoxy-2-fluoroprop-1-enyl)-1-(4-ethoxyphenyl)cyclopropane

Product 1

HCID 544502131-(4-Ethoxyphenyl)-1-(2-fluoro-3-(4-fluoro-3-phenoxyphenyl)-prop-1-enyl)cyclopropaneYield 12.4%

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 (0.246 g), tetrahydrofuran (2 ml) and magnesium (21 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(4-ethoxyphenyl)cyclopropane (Example 18) (0.176 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-ethoxyphenyl)-1-(2-fluoro-3-(4-fluoro-3-phenoxyphenyl)-prop-1-enyl)cyclopropane (32 mg, 12%).

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-9b9ec7ea0c1a44eeb8243735f7a139fb
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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