Magnesium → 4-(4-Ethoxyphenyl)-2-fluoro-1-(4-fluoro-3-phenoxyphenyl)-4-methylpent-2-ene

HRID 1418071Notes

Reaction equation

HRID 1418071 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]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH3:35])=[CH:29][CH:28]=1)([CH3:26])[CH3:25])(=O)C>O1CCCC1>[CH2:34]([O:33][C:30]1[CH:31]=[CH:32][C:27]([C:24]([CH3:25])([CH3:26])[CH:23]=[C:22]([F:36])[CH2:21][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:4]=2)=[CH:28][CH:29]=1)[CH3:35]

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 11076399Benzene, 4-bromo-1-fluoro-2-phenoxy-HCID 543050034-(4-Ethoxyphenyl)-2-fluoro-4-methylpent-2-enyl acetate

Product 1

HCID 539241884-(4-Ethoxyphenyl)-2-fluoro-1-(4-fluoro-3-phenoxyphenyl)-4-methylpent-2-eneYield 20.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 16 was repeated using a Grignard reagent, prepared from 4-fluoro-3-phenoxyphenyl bromide (0.28 g), tetrahydrofuran (2 ml) and magnesium (20 mg), and 4-(4-ethoxyphenyl)-2-fluoro-4-methylpent-2-enyl acetate (Example 14) (60 mg). 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: 5% water in methanol; flow rate: 3 ml/min) to give the title compound (18 mg, 20%).

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-7e2cdfb06bef41c2bdd76a5eeef3fcc3
Source dataset
uspto-grants-1999_03
Patent number
US05880162

Reaction notes

Loading…