{3-[(3-Chloro-5-cyanophenyl)oxy]-2-fluoro-4-nitrophenyl}acetic acid → 3-Chloro-5-[(2-fluoro-3-methyl-6-nitrophenyl)oxy]benzonitrile

HRID 1874780Notes

Reaction equation

HRID 1874780 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([F:24])=[C:13]([CH2:20]C(O)=O)[CH:14]=[CH:15][C:16]=2[N+:17]([O-:19])=[O:18])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1>CC#N>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([O:10][C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13]([CH3:20])[C:12]=2[F:24])[CH:3]=1)[C:8]#[N:9]

Participants

3

Reactant 1

HCID 59451579{3-[(3-Chloro-5-cyanophenyl)oxy]-2-fluoro-4-nitrophenyl}acetic acid

Product 1

HCID 594515483-Chloro-5-[(2-fluoro-3-methyl-6-nitrophenyl)oxy]benzonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude {3-[(3-chloro-5-cyanophenyl)oxy]-2-fluoro-4-nitrophenyl}acetic acid was dissolved in CH3CN (50 mL) and Cu2O (0.65 g, 4.5 mmol) was added. A condenser was attached and the heterogeneous mixture was heated to reflux for 2 h. The reaction mixture was cooled to RT, filtered through Celite and the solvent evaporated. Purification was accomplished by column chromatography (hexane/EtOAc) to afford the title compound (6.0 g, 87%), which solidified upon standing. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.98 (dd, 1H), 7.81 (d, 1H), 7.60 (d, 2H), 7.52 (t, 1H), 2.37 (d, 3H).

Workup

  1. customA condenser was attached
  2. temperaturethe heterogeneous mixture was heated
  3. temperatureto reflux for 2 h
  4. filtrationfiltered through Celite
  5. customthe solvent evaporated
  6. customPurification

Sources & evidence

ORD record
ord-2641825a6ea347cc826752d5abda73d1
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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