Potassium Carbonate → 4-(4-Acetyl-3-chlorophenoxy)benzonitrile

HRID 1095899

Reaction equation

HRID 1095899 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][C:16](F)=[CH:15][C:14]=1[Cl:20])=[O:12].C([O-])([O-])=O.[K+].[K+].CCCCCCC.CCOC(C)=O>CC(N(C)C)=O.O>[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:15][C:14]=1[Cl:20])(=[O:12])[CH3:10]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 27365072'-Chloro-4'-fluoroacetophenoneHCID 21899848Ethylacetate heptane

Product 1

HCID 643355014-(4-Acetyl-3-chlorophenoxy)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution 4-cyanophenol (CAS Reg. No. 767-00-0, 1.2 g), 2-chloro-4-fluoroacetophenone (CAS Reg. No. 700-35-6, 1.7 g) in DMA (10 ml) was added K2CO3 (1.66 g). The mixture is refluxed for 5 h. TLC (heptane/EtOAc 2:1) showed complete conversion. Water was added and the mixture was extracted with DCM. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (1.8 g) as yellow oil. MS (m/e)=272.2 [M+H+].

Workup

  1. temperatureThe mixture is refluxed for 5 h
  2. extractionthe mixture was extracted with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated to an oil
  5. customThe residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2)

Sources & evidence

ORD record
ord-dc8398acd11a40ffbe7b23aa940ad840
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Linked notes

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