Isopropyl iodide → HCID 43657408, compound

HRID 715691Notes

Reaction equation

HRID 715691 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].[CH:11](I)([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 27829443-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 43657408HCID 43657408, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.0 g 3-Fluoro-4-hydroxy-benzonitrile, 7.3 mL isopropyl iodide and 6.05 g potassium carbonate were placed in 54 mL acetone and heated to reflux where the reaction was maintained for 24 h. After this time, the mixture was cooled to ambient temperature and concentrated under reduced pressure. The material that remained was partitioned between ethyl acetate and water and the aqueous phase was removed and extracted with additional ethyl acetate. The combined organics were dried, filtered and the solvent was removed from the filtrate under reduced pressure to give the title compound that was used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux where the reaction
  3. temperaturewas maintained for 24 h
  4. concentrationconcentrated under reduced pressure
  5. customThe material that remained was partitioned between ethyl acetate and water
  6. customthe aqueous phase was removed
  7. extractionextracted with additional ethyl acetate
  8. customThe combined organics were dried
  9. filtrationfiltered
  10. customthe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-83dcf9b847f84eec93bc5f8fd2589558
Source dataset
uspto-grants-2015_11
Patent number
US09187478B2

Reaction notes

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