3-Bromodiphenyl ether → 1-(4-Ethoxy-phenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropane

HRID 963826Notes

Reaction equation

HRID 963826 reaction equation
[O:1]([C:8]1[CH:9]=[C:10](Br)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].C(O[CH2:20][C:21]([F:35])=[CH:22][C:23]1([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[CH:28][CH:27]=2)[CH2:25][CH2:24]1)(=O)C>O1CCCC1>[CH2:33]([O:32][C:29]1[CH:30]=[CH:31][C:26]([C:23]2([CH:22]=[C:21]([F:35])[CH2:20][C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:9]=3)[CH2:24][CH2:25]2)=[CH:27][CH:28]=1)[CH3:34]

Participants

5

Reactant 3

HCID 961653-Bromodiphenyl etherHCID 5462224MagnesiumHCID 543885951-(3-Acetoxy-2-fluoroprop-1-enyl)-1-(4-ethoxyphenyl)cyclopropane

Product 1

HCID 543416001-(4-Ethoxy-phenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropaneYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 25 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (2.35 g), tetrahydrofuran (10 ml) and magnesium (0.21 g) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(4-ethoxyphenyl)cyclopropane (Example 18) (0.6 g). The residue after evaporation was purified by column chromatography (solvent: diethyl ether/hexane; 5:95) to afford 1-(4-ethoxy-phenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropane (0.34 g, 41%)

Workup

  1. customThe residue after evaporation
  2. customwas purified by column chromatography (solvent: diethyl ether/hexane; 5:95)

Sources & evidence

ORD record
ord-439e880269a74fe69b4f8035b46548ff
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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