Water → 4-Chloro-2-fluoro-5-isopropoxy-nitrobenzene

HRID 1086677Notes

Reaction equation

HRID 1086677 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[CH:19](I)([CH3:21])[CH3:20].O>C(#N)C>[Cl:1][C:2]1[C:3]([O:12][CH:19]([CH3:21])[CH3:20])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-

Product 1

HCID 131089864-Chloro-2-fluoro-5-isopropoxy-nitrobenzeneYield 57.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-4-fluoro-5-nitrophenol (19.1 g) in acetonitrile (100 ml), there was added anhydrous potassium carbonate (8 g). After stirring at room temperature for several minutes, isopropyl iodide (25 g) was added thereto, and the resultant mixture was heated under reflux for 3 hours. After being allowed to cool to room temperature, water was added thereto, and the reaction mixture was extracted with ether. The ether extract was washed with a 5% aqueous sodium hydroxide solution and water in this order, dried over anhydrous magnesium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethanol to obtain 13.5 g of 4-chloro-2-fluoro-5-isopropoxynitrobenzene. M.P., 61.3°62.4° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureto cool to room temperature
  3. extractionthe reaction mixture was extracted with ether
  4. extractionThe ether extract
  5. washwas washed with a 5% aqueous sodium hydroxide solution and water in this order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationsubjected to filtration
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-60f67042da1347ad8d0b3085043b16de
Source dataset
uspto-grants-1991_07
Patent number
US05030761

Reaction notes

Loading…