3,4-Dichlorophenol → 2-(3,4-Dichlorophenoxy)-5-Fluoro-Benzonitrile

HRID 6898

Reaction equation

HRID 6898 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].F[C:17]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:18]=1[C:19]#[N:20]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][C:17]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:18]=1[C:19]#[N:20]

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 1235582,5-Difluorobenzonitrile

Product 1

HCID 220192752-(3,4-Dichlorophenoxy)-5-Fluoro-Benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A flame-dried flask containing N2 inlet and magnetic stirrer was charged with 2.9 g (18 mmol) of 3,4-dichlorophenol, 6.2 g (45 mmol) of potassium carbonate and 50 mL of anhydrous DMF. With stirring, 2.08 g (15 mmol) of 2,5-difluorobenzonitrile (Aldrich Chem. Co.) was added and the mixture was heated overnight at 105° C., cooled to room temperature and partitioned between water and EtOAc. The aqueous layer was reextracted with EtOAc and the combined organic layers were successively washed with 2N NaOH, water and saturated aqueous NaCl. After drying with MgSO4, the solvent was removed to give the title product as a light brown oil which slowly solidified, 3.5 g.

Workup

  1. additionA flame-dried flask containing N2 inlet and magnetic stirrer
  2. temperaturecooled to room temperature
  3. custompartitioned between water and EtOAc
  4. washthe combined organic layers were successively washed with 2N NaOH, water and saturated aqueous NaCl
  5. dry with materialAfter drying with MgSO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-46b34f726ee24169b4da1dd46149cf32
Source dataset
uspto-grants-2006_08
Patent number
US07084165B2

Linked notes

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