3-Bromodiphenyl ether → 1-(2-Fluoro-3-(3-phenoxyphenyl)prop-1-enyl)-1-(3,4-methylenedioxyphenyl)cyclopropane

HRID 963830Notes

Reaction equation

HRID 963830 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]3[O:32][CH2:33][O:34][C:28]=3[CH:27]=2)[CH2:25][CH2:24]1)(=O)C>O1CCCC1>[F:35][C:21]([CH2:20][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=1)=[CH:22][C:23]1([C:26]2[CH:31]=[CH:30][C:29]3[O:32][CH2:33][O:34][C:28]=3[CH:27]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 961653-Bromodiphenyl etherHCID 5462224MagnesiumHCID 541495881-(3-Acetoxy-2-fluoroprop-1-enyl)-1-(3,4-methylenedioxyphenyl)cyclopropane

Product 1

HCID 541885771-(2-Fluoro-3-(3-phenoxyphenyl)prop-1-enyl)-1-(3,4-methylenedioxyphenyl)cyclopropaneYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 25 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.40 g), tetrahydrofuran (2 ml) and magnesium (30 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(3,4-methylene-dioxyphenyl)cyclopropane (Example 22) (0.32 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 5:95) to afford 1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)-1-(3,4-methylenedioxyphenyl)cyclopropane (82 mg, 19%).

Workup

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

Sources & evidence

ORD record
ord-d920a2d696ce47eb93ba17945d93a10e
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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