3-Chlorophenol → 2-(3-Chlorophenoxy)-4-methyl-benzonitrile

HRID 379028Notes

Reaction equation

HRID 379028 reaction equation
F[C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Cl:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.CCOC(C)=O>[Cl:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 79333-ChlorophenolHCID 10796Cesium carbonateHCID 27784432-Fluoro-4-methylbenzonitrile

Product 1

HCID 216970852-(3-Chlorophenoxy)-4-methyl-benzonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-fluoro-4-methylbenzonitrile (356mg, 3.96 mmol) and 3-chlorophenol (439 μL, 4.16 mmol) in 10 mL of DMSO was added Cs2CO3 (2.58 g, 7.92 mmol). The solution was heated at 80° C. for 4 h. The solution was diluted with EtOAc and was washed with Sat. NaHCO3 solution, water, and brine. The organics were dried (MgSO4), filtered, and concentrated in vacuo to give the title compound without further purification.

Workup

  1. washwas washed with Sat. NaHCO3 solution, water, and brine
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f765954de40c462980308c3bbef788c8
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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