Potassium Carbonate → (5-Chloro-2-isopropyl-4-methoxy-phenoxy)-acetonitrile

HRID 81752

Reaction equation

HRID 81752 reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH:9]([CH3:11])[CH3:10])=[C:6]([OH:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:21][C:22]#[N:23]>CN(C=O)C>[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH:9]([CH3:11])[CH3:10])=[C:6]([CH:7]=1)[O:8][CH2:21][C:22]#[N:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69356IodoacetonitrileHCID 595986685-Chloro-2-isopropyl-4-methoxy-phenol

Product 1

HCID 59598662(5-Chloro-2-isopropyl-4-methoxy-phenoxy)-acetonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-chloro-2-isopropyl-4-methoxy-phenol (10.36 g, 51.6 mmol) in 40 mL DMF was added K2CO3 (8.55 g, 62.0 mmol) and the mixture was heated to 65° C. After 15 minutes iodoacetonitrile (9.05 g, 54.2 mmol) was added and the mixture was heated to 80° C. for 1 hour. The mixture was cooled, poured into an ice/H2O mixture and extracted with 1:1 toluene/hexane. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by passing through a short plug of silica to afford (5-chloro-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (11.97 g, 97%) as a white solid.

Workup

  1. temperaturethe mixture was heated to 80° C. for 1 hour
  2. temperatureThe mixture was cooled
  3. extractionextracted with 1:1 toluene/hexane
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-aee3b7f032e34da1bcd1818b9991c4b2
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Linked notes

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