{3-[(3-Bromo-5-chlorophenyl)oxy]-2-fluoro-4-nitrophenyl}acetic acid → 2-[(3-Bromo-5-chlorophenyl)oxy]-3-fluoro-4-methyl-1-nitrobenzene

HRID 1874934Notes

Reaction equation

HRID 1874934 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:11]([F:23])=[C:12]([CH2:19]C(O)=O)[CH:13]=[CH:14][C:15]=2[N+:16]([O-:18])=[O:17])[CH:5]=[C:6]([Cl:8])[CH:7]=1>CC#N>[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:11]([F:23])=[C:12]([CH3:19])[CH:13]=[CH:14][C:15]=2[N+:16]([O-:18])=[O:17])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 1

HCID 68488957{3-[(3-Bromo-5-chlorophenyl)oxy]-2-fluoro-4-nitrophenyl}acetic acid

Product 1

HCID 684855692-[(3-Bromo-5-chlorophenyl)oxy]-3-fluoro-4-methyl-1-nitrobenzeneYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude {3-[(3-bromo-5-chlorophenyl)oxy]-2-fluoro-4-nitrophenyl}acetic acid was dissolved in CH3CN (150 mL) and Cu2O (1.18 g, 8.22 mmol) was added. A condenser was attached and the heterogeneous mixture was heated to reflux for 3 h. The reaction mixture was cooled to RT, filtered through Celite and the solvent evaporated. The crude brown oil was purified by column chromatography (5% to 70% EtOAc/hexanes gradient) to afford the title compound (13.0 g, 88% over three steps) as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.94-7.91 (m, 1H), 7.49-7.45 (m, 2H), 7.22 (s, 1H), 7.14 (s, 1H), 2.34 (s, 3H).

Workup

  1. customA condenser was attached
  2. temperaturethe heterogeneous mixture was heated
  3. temperatureto reflux for 3 h
  4. filtrationfiltered through Celite
  5. customthe solvent evaporated
  6. customThe crude brown oil was purified by column chromatography (5% to 70% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-f43717087206424192c8aa081e233716
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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