Water → 4-(4-Chloro-2-fluoro-phenoxy)-3-fluoro-benzonitrile

HRID 1406329Notes

Reaction equation

HRID 1406329 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.CC(C)([O-])C.[K+].[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1F)[C:20]#[N:21].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:24]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=2[F:16])=[C:4]([F:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1819754-Chloro-2-fluorophenolHCID 5872033,4-DifluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 667894214-(4-Chloro-2-fluoro-phenoxy)-3-fluoro-benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1.6 mL (15 mmol) of 4-chloro-2-fluorophenol and 1.68 g (15 mmol) of potassium tert. butoxide in 10 mL DMSO was stirred for one hour at ambient temperature. Then 2.1 g (15 mmol) of 3,4-difluoro-benzonitrile were added and the mixture was stirred overnight at 60° C. The mixture was then combined with approx. 50 mL water, then extracted three times with 30 ml of ethyl acetate. The organic extracts were washed with sodium chloride solution, dried on sodium sulphate and evaporated down. The product thus obtained was reacted further without any further purification.

Workup

  1. extractionextracted three times with 30 ml of ethyl acetate
  2. washThe organic extracts were washed with sodium chloride solution
  3. customdried on sodium sulphate
  4. customevaporated down
  5. customThe product thus obtained
  6. customwas reacted further without any further purification

Sources & evidence

ORD record
ord-b1a59db637c64b4eac6a30a68468a1c6
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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