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

HRID 1418069Notes

Reaction equation

HRID 1418069 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]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[CH:28][CH:27]=1)([CH3:25])[CH3:24])(=O)C>O1CCCC1>[CH2:33]([O:32][C:29]1[CH:30]=[CH:31][C:26]([C:23]([CH3:24])([CH3:25])[CH:22]=[C:21]([F:35])[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:27][CH:28]=1)[CH3:34]

Participants

5

Reactant 3

HCID 961653-Bromodiphenyl etherHCID 5462224MagnesiumHCID 543050034-(4-Ethoxyphenyl)-2-fluoro-4-methylpent-2-enyl acetate

Product 1

HCID 539502474-(4-Ethoxyphenyl)-2-fluoro-4-methyl-1-(3-phenoxyphenyl)pent-2-eneYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 16 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.31 g), tetrahydrofuran (2 ml) and magnesium (24 mg), and 4-(4-ethoxyphenyl)-2-fluoro-methylpent-2-enyl acetate (Example 14) (70 mg). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) to give the title compound (44 mg, 45%/).

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-c845f0fcbb6c4a5c9db8db0ae7d3b306
Source dataset
uspto-grants-1999_03
Patent number
US05880162

Reaction notes

Loading…