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

HRID 2041162Notes

Reaction equation

HRID 2041162 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].[CH2:11](Br)[CH:12]=[CH2:13].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.CCOC(C)=O>[CH2:13]([O:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Br:1])[CH:12]=[CH2:11]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 753413-Bromo-4-hydroxybenzonitrile

Product 1

HCID 576559564-Allyloxy-3-bromo-benzonitrile

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix 3-bromo-4-hydroxy-benzonitrile (1.520 g, 8.0 mmol), allyl bromide (1.161g, 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-cad3beaa4fcf475cbbb26aa0f69f6f7c
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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