2,4-Dichlorophenol → 2-(2,4-Dichlorophenoxy)benzonitrile

HRID 1642237Notes

Reaction equation

HRID 1642237 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].F[C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 11430Potassium CarbonateHCID 678552-Fluorobenzonitrile

Product 1

HCID 27770202-(2,4-Dichlorophenoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

AMR01045 A mixture of 2,4-dichlorophenol (2.00 g, 12.27 mmol), 2-fluorobenzonitrile (1.49 g, 12.27 mmol) and potassium carbonate (1.7 g, 12.27 mmol) in DMF (10 mL) was stirred under reflux for 1.5 h. After removal of DMF, the residue was dissolved in DCM and washed with NaOH (5%, 3×20 mL) and brine. The organic layer was dried (MgSO4), filtered and evaporated and 2-(2,4-dichlorophenoxy)benzonitrile was obtained as an oil (2.73 g, 84%), which was used in the next step without further purification. Rf: 0.64 (DCM) 1H NMR (300 MHz, CDCl3) δ 6.73 (1H, dd, J=8.4 Hz), 7.13 (1H, d, J=8.7 Hz), 7.22 (1H, td, J=8.7, 1.0 Hz), 7.35 (1H, dd, J=8.7, 2.4 Hz), 7.56 (1H, d, J=2.4 Hz) and 7.73 (1H, dd, J=7.5, 2.7 Hz).

Workup

  1. temperatureunder reflux for 1.5 h
  2. customAfter removal of DMF
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with NaOH (5%, 3×20 mL) and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-46a8b4528f2541b48c9d17f872d16241
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

Loading…