4-Chlorophenol → 6-(4-Chloro-phenoxy)-hexanenitrile

HRID 2097365Notes

Reaction equation

HRID 2097365 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 810936-Bromohexanenitrile

Product 1

HCID 231324196-(4-Chloro-phenoxy)-hexanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

6-Bromohexanenitrile (2.65 mL, 20 mmol) and 4-chlorophenol (2.57 g, 20 mmol) were dissolved in DMF (50 mL). After addition of K2CO3 (5.53 g, 40 mmol) the mixture was stirred at 95° C. for 3 h. The solvent was evaporated under reduced pressure and the residue was partitioned between water (80 mL) and Et2O (200 mL). The org. layer was separated, washed with pH 7 phosphate buffer solution (1×50 ml), dried over Na2SO4, filtered and the solvent was removed under reduced pressure to give the title compound, pure enough for further reactions.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between water (80 mL) and Et2O (200 mL)
  3. customlayer was separated
  4. washwashed with pH 7 phosphate buffer solution (1×50 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4c37f378066043749d2921abb249738d
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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