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

HRID 963828Notes

Reaction equation

HRID 963828 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:33])=[CH:22][C:23]1([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:25][CH2:24]1)(=O)C>O1CCCC1>[F:33][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:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 961653-Bromodiphenyl etherHCID 5462224MagnesiumHCID 536458661-(3-Acetoxy-2-fluoroprop-1-enyl)-1-(4-fluorophenyl)cyclopropane

Product 1

HCID 190833411-(2-Fluoro-3-(3-phenoxyphenyl)prop-1-enyl)-1-(4-fluorophenyl)cyclopropaneYield 27.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 25 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.38 g), tetrahydrofuran (2 ml) and magnesium (28 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(4-fluorophenyl)cyclopropane (Example 20) (0.12 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: phenyl; solvent: methanol; flow rate: 2 ml/min) to afford 1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)-1-(4 -fluorophenyl)cyclopropane (48 mg, 27%).

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-fbb18802076347768ec4ef318ae355a6
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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