Isopropyl iodide → HCID 10610340, compound

HRID 612617Notes

Reaction equation

HRID 612617 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].C([O-])([O-])=O.[K+].[K+].[CH:17](I)([CH3:19])[CH3:18]>CC(=O)CC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:17]([CH3:19])[CH3:18])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 3479554-Bromo-3-methoxyphenol

Product 1

HCID 10610340HCID 10610340, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a stirred suspension of 4-bromo-3-methoxyphenol (2.03 g, 10 mmol) and K2CO3 (1.38 g, 10 mmol) in 2-butanone (70 mL) at ambient temperature under argon is added dropwise isopropyl iodide (2.21 g, 13.3 mmol). The resulting mixture is heated and stirred under reflux for 17 hours. The mixture is allowed to cool to ambient temperature then is filtered and concentrated by evaporation of the solvent. The residue is partitioned between Et2O and H2O. The Et2O layer is extracted with 5% NaOH (2×50 mL), washed with brine, and dried over MgSO4. The solvent is evaporated and the resulting residue is purified by flash chromatography (5% EtOAc/hexane) to afford the desired compound as a pale yellow oil. 2.13 g (87%).

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureunder reflux for 17 hours
  3. filtrationthen is filtered
  4. concentrationconcentrated by evaporation of the solvent
  5. customThe residue is partitioned between Et2O and H2O
  6. extractionThe Et2O layer is extracted with 5% NaOH (2×50 mL)
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. customThe solvent is evaporated
  10. customthe resulting residue is purified by flash chromatography (5% EtOAc/hexane)

Sources & evidence

ORD record
ord-ffc23aedb54f4b85b51ff6275a2458e4
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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