3-Bromodiphenyl ether → 4-(4-Chlorophenyl)-2-fluoro-4-methyl-1-(3-phenoxyphenyl)pent-2-ene

HRID 1418068Notes

Reaction equation

HRID 1418068 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]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)([CH3:25])[CH3:24])(=O)C>O1CCCC1>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([C:23]([CH3:25])([CH3:24])[CH:22]=[C:21]([F:33])[CH2:20][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 961653-Bromodiphenyl etherHCID 5462224MagnesiumHCID 538048424-(4-Chlorophenyl)-2-fluoro-4-methylpent-2-enyl acetate

Product 1

HCID 539352784-(4-Chlorophenyl)-2-fluoro-4-methyl-1-(3-phenoxyphenyl)pent-2-eneYield 22.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 16 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.19 g), tetrahydrofuran (2 ml) and magnesium (22 g), and 4-(4-chlorophenyl)-2-fluoro-4-methylpent-2-enyl acetate (Example 13) (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: C18; solvent: methanol; flow rate: 3 ml/min; to give the title compound (38 mg, 22%).

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-4e0f95fca1b44954909046f7f63f93b9
Source dataset
uspto-grants-1999_03
Patent number
US05880162

Reaction notes

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