Potassium Iodide → 4-Allyloxy-3-bromo-benzonitrile

HRID 911275Notes

Reaction equation

HRID 911275 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].[C:11](=O)([O-])[O-].[K+].[K+].[I-].[K+].CCO[C:22]([CH3:24])=O>CC(C)=O>[CH2:11]([O:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Br:1])[CH:22]=[CH2:24]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 753413-Bromo-4-hydroxybenzonitrile

Product 1

HCID 576559564-Allyloxy-3-bromo-benzonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Mix 3-bromo-4-hydroxy-benzonitrile (1.520 g, 8.0 mmol), alkyl bromide (1.161 g, 9.6 mmol), potassium carbonate (3.317 g, 24 mmol) and potassium iodide (133 mg, 0.1 mmol) in acetone (80 mL). Heat the mixture to reflux for 12 h. Cool to ambient temperature, add EtOAc, wash the organic layer with water, and extract the aqueous layer twice with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate. Purify by chromatography on silica gel eluting with EtOAc/hexane (1:8) to obtain the desired intermediate.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 12 h
  3. washwash the organic layer with water
  4. extractionextract the aqueous layer twice with EtOAc
  5. dry with materialDry the combined organic extracts over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify by chromatography on silica gel eluting with EtOAc/hexane (1:8)

Sources & evidence

ORD record
ord-d2d7f99889cf4741881c7184e504e33b
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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