2-Chlorophenol → 2-Chloro-4-(2-chloro-phenoxy)-benzonitrile

HRID 1406349Notes

Reaction equation

HRID 1406349 reaction equation
[Cl: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:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Cl:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 72452-ChlorophenolHCID 11430Potassium CarbonateHCID 1090002-Chloro-4-fluorobenzonitrile

Product 1

HCID 551532072-Chloro-4-(2-chloro-phenoxy)-benzonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 1.17 g (7.54 mmol) of 2-chloro-4-fluorobenzonitrile and 0.97 g (7.54 mmol) of 2-chlorophenol in 40 mL DMSO was combined with 3.2 g (23.16 mmol) of potassium carbonate and stirred overnight at 120° C. Then the mixture was evaporated to dryness in vacuo, the residue was mixed with water and extracted with ethyl acetate. The extracts were washed with water and saturated sodium chloride solution, dried and evaporated down. The crude product thus obtained was purified by column chromatography (silica gel, dichloromethane).

Workup

  1. customThen the mixture was evaporated to dryness in vacuo
  2. additionthe residue was mixed with water
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water and saturated sodium chloride solution
  5. customdried
  6. customevaporated down

Sources & evidence

ORD record
ord-dfa3c35c439947cd94477e6f3734c4a8
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

Loading…