Potassium Carbonate → 2-(4-Chloro-2-methoxyphenoxy)-6-fluorobenzonitrile

HRID 2176992Notes

Reaction equation

HRID 2176992 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=2[C:4]#[N:5])=[C:14]([O:19][CH3:20])[CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 280504-ChloroguaiacolHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 669242192-(4-Chloro-2-methoxyphenoxy)-6-fluorobenzonitrileYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2,6-difluorobenzonitrile (100 mg; 0.72 mmol) and 4-chloro-2-methoxyphenol (114 mg; 0.72 mmol) in anhydrous DMF (5 mL) is added potassium carbonate (50 mg; 0.36 mmol). The reaction mixture is heated to 70° C. overnight. After allowing to room temperature, the solvent is removed under vacuum and the resulting solid is partitioned between ethyl acetate and water. The organics are separated and dried over magnesium sulfate. The solvent is removed to give 145 milligrams of 2-(4-chloro-2-methoxyphenoxy)-6-fluorobenzonitrile.

Workup

  1. customAfter allowing to room temperature
  2. customthe solvent is removed under vacuum
  3. customthe resulting solid is partitioned between ethyl acetate and water
  4. customThe organics are separated
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is removed

Sources & evidence

ORD record
ord-bbc32e0cdc114f3ab9223a4e4a7891c6
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

Loading…