Isopropyl iodide → 4-Fluoro-2-isopropoxy-1-nitrobenzene

HRID 1188896Notes

Reaction equation

HRID 1188896 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.I[CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH:13]([CH3:15])[CH3:14])[CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 106318324-Fluoro-2-isopropoxy-1-nitrobenzeneYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-fluoro-2-nitrophenol (91.0 g), 2-iodopropane (103.4 g), potassium carbonate (146 g) and N,N-dimethylformamide (600 mL) was stirred at 50° C. for 3.5 h. The mixture was concentrated under reduced pressure and water was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by basic silica gel column chromatography (ethyl acetate/hexane=0/100 to 30/70, volume ratio) to give the title compound (75.4 g, 65%) as a yellow oil.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/hexane=0/100 to 30/70, volume ratio)

Sources & evidence

ORD record
ord-a0121e791f604750b19ca7a6c285a8c3
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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