4-Chlorophenol → 2-(4-Chlorophenoxy)benzonitrile

HRID 1642242Notes

Reaction equation

HRID 1642242 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.F[C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#[N:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 678552-Fluorobenzonitrile

Product 1

HCID 141307012-(4-Chlorophenoxy)benzonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chlorophenol (2.00 g, 15.56 mmol), 2-fluorobenzonitrile (1.88 g, 15.56 mmol) and potassium carbonate (2.15 g, 15.56 mmol) in DMF (10 mL) was stirred under reflux for 4 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 to give 2-(4-chlorophenoxy)benzonitrile (3.2 g, 90%) as a white solid, mp 84-86° C., which was used in the next step without further purification. Rf: 0.62 (DCM) 1H NMR (270 MHz, CDCl3) δ 6.86 (1H, dd, J=8.4, 0.8 Hz), 7.02 (2H, AA′BB′), 7.15 (1H, td, J=7.7, 1.0 Hz), 7.35 (2H, AA′BB′), 7.48 (1H, m) and 7.65 (1H, dd, J=7.7, 1.5 Hz). LC/MS (APCI) tr=4.66 min, m/z 232.28 (31), 230.27 (M++H, 100).

Workup

  1. temperatureunder reflux for 4 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-a89379f844724117b3bb7d763e0e09c0
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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