Potassium Carbonate → HCID 57678433, compound

HRID 491494Notes

Reaction equation

HRID 491494 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([I:10])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]#[N:21]>CC(C)=O>[I:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([I:10])=[CH:4][C:3]=1[O:11][CH2:19][C:20]#[N:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 57678422HCID 57678422, compound

Product 1

HCID 57678433HCID 57678433, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

2,5-Diiodo-4-methoxy-phenol (2.8 g, 7.5 mmol) and potassium carbonate (2.1 g) were added to 30 mL of stirring acetone at room temperature and under nitrogen. Bromoacetonitrile (0.575 mL, 8.25 mmol) was added, and the reaction mixture was heated to 60° C. and stirred under nitrogen for 8 hours, then stirred for 18 hours under nitrogen at room temperature. The reaction mixture concentrated under reduced pressure, and the residue was poured into water and extracted into EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed on 150 g of flash silica (5%-20% EtOAc/hexanes) to give 2.86 g of (2,5-Diiodo-4-methoxy-phenoxy)-acetonitrile, MS (M+H)=416.

Workup

  1. stirringstirred for 18 hours under nitrogen at room temperature
  2. concentrationThe reaction mixture concentrated under reduced pressure
  3. additionthe residue was poured into water
  4. extractionextracted into EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on 150 g of flash silica (5%-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-84c5416d841e40e09f5ec4ae5ae2274f
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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