Isopropyl iodide → 2-Bromo-4-nitro-1-[(propan-2-yl)oxy]benzene

HRID 1420825Notes

Reaction equation

HRID 1420825 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].I[CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:13]([O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Br:1])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 221092-Bromo-4-nitrophenol

Product 1

HCID 187825712-Bromo-4-nitro-1-[(propan-2-yl)oxy]benzeneYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-bromo-4-nitrophenol (Description 40, 2.5 g), 2-iodopropane (2.2 g) and potassium carbonate (5 g) in acetone (30 ml) was heated under reflux for 18 h. The solvent was evaporated under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/EtOAc (90:10) to give the title compound (2.8 g, 94%). 1H NMR (250 MHz, CDCl3) δ8.46 (1H, s), 8.20 (1H, m), 6.93 (1H, m), 4.75 (1H, m), and 1.42 (6H, d, J 7.5 Hz).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customThe solvent was evaporated under reduced pressure, water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by flash column chromatography on silica gel
  10. washeluting with hexane/EtOAc (90:10)

Sources & evidence

ORD record
ord-636b5bf3265446f7bd753568e9000839
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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