Ethyl Acetate → 4-(4-Amino-2-chlorophenoxy)-2-fluorobenzonitrile

HRID 16426

Reaction equation

HRID 16426 reaction equation
[F:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[OH:19])[NH2:15].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C>[NH2:15][C:14]1[CH:16]=[CH:17][C:18]([O:19][C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=2)=[C:12]([Cl:11])[CH:13]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 775452,4-DifluorobenzonitrileHCID 775784-Amino-2-chlorophenol

Product 1

HCID 179793474-(4-Amino-2-chlorophenoxy)-2-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.00 g (14.4 mmol) of 2,4-difluorobenzonitrile, 2.06 g (14.4 mmol) of 3-chloro-4-hydroxyaniline and 3.97 g (28.8 mmol) of potassium carbonate in 20 ml of acetonitrile are heated at RF for one hour. Ethyl acetate is added, the mixture is filtered and the solvent is removed under reduced pressure. The residue is purified by column chromatography (silica gel 60), giving the product which is a regioisomer mixture with a ratio of 62:38.

Workup

  1. filtrationthe mixture is filtered
  2. customthe solvent is removed under reduced pressure
  3. customThe residue is purified by column chromatography (silica gel 60)
  4. customgiving the product which

Sources & evidence

ORD record
ord-469b7561ac284cd882eeac1cf9b3c0ae
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Linked notes

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