Water → 5-Fluoro-2-nitroanisole

HRID 1282080Notes

Reaction equation

HRID 1282080 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([OH:10])[CH:9]=1.[CH3:14]I.O>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[F:3][C:4]1[CH:5]=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([O:10][CH3:14])[CH:9]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 99375-Fluoro-2-nitrophenolHCID 24758Sodium hydride

Product 1

HCID 27792505-Fluoro-2-nitroanisole

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (1.3 g) in dimethylformamide (10 ml) was added a solution of 5-fluoro-2-nitrophenol (5.0 g) in dimethylformamide (20 ml)under ice-cooling. This reaction mixture was stirred at room temperature for 1 hr. To this solution was added methyl iodide (2.0 ml) and the mixture was left standing overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with an aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a red solid. This solid was subjected to silica gel column chromatography (developing solvent; hexane:ethyl acetate=4:1) to give the title compound (4.3 g) as a yellow solid.

Workup

  1. temperaturecooling
  2. waitthe mixture was left
  3. waitstanding overnight
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with an aqueous sodium hydroxide solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customto give a red solid

Sources & evidence

ORD record
ord-f1825b366de14c90a4c7239fd145c51e
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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