2-Chloro-4-fluorophenol → 2-Methyl-4-(2'-chloro-4'-fluorophenoxy)benzonitrile

HRID 436981Notes

Reaction equation

HRID 436981 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.[K].[Cl:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[OH:20]>CC(N(C)C)=O>[CH3:10][C:4]1[CH:3]=[C:2]([O:20][C:14]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=2[Cl:12])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 748142-Chloro-4-fluorophenolHCID 1427424-Chloro-2-methylbenzonitrileHCID 5462222Potassium

Product 1

HCID 214295622-Methyl-4-(2'-chloro-4'-fluorophenoxy)benzonitrileYield 96.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A stirred solution of 4-chloro-2-methylbenzonitrile (4.7 g., 0.03 mole) and the potassium salt of 2-chloro-4-fluorophenol (5.54 g., 0.03 mole) in 40 ml of dimethyl acetamide was heated for 48 hours at 150° C. The cooled reaction mixture was diluted with 200 ml. of water to precipitate a brown oil. An ether extract yielded 7.6 g of 2-methyl-4-(2'-chloro-4'-fluorophenoxy)benzonitrile as a brown oil in about 90% purity.

Workup

  1. customThe cooled reaction mixture
  2. additionwas diluted with 200 ml
  3. customof water to precipitate a brown oil
  4. extractionAn ether extract

Sources & evidence

ORD record
ord-99c235b665f1481a9dcb14e3e3d0fe7b
Source dataset
uspto-grants-1977_06
Patent number
US04029493

Reaction notes

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