Methyl iodide → 5-Fluoro-2-nitroanisole

HRID 2222124Notes

Reaction equation

HRID 2222124 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.[C:12](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH3:12])[CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 27792505-Fluoro-2-nitroanisole

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

20 g (126 mmol) 5-fluoro-2-nitro-phenol are dissolved in 300 ml acetone. 22.6 g (163 mmol) potassium carbonate are added and the mixture is stirred for 30 min at 20° C. Over a period of 10 min, 9.4 ml (150 mmol) methyl iodide, diluted in 50 ml acetone, is added and the mixture is stirred for a further 18 h at 20° C. Then it is left for another 12 h at 65° C. with stirring. The solvent is eliminated in vacuo, the residue is taken up in water and extracted three times with ethyl acetate. Then the combined organic phases are extracted three times with 10% aqueous sodium carbonate solution. The organic phase is dried over magnesium sulphate. The solvent is eliminated in vacuo.

Workup

  1. waitOver a period of 10 min
  2. additionis added
  3. stirringthe mixture is stirred for a further 18 h at 20° C
  4. waitThen it is left for another 12 h at 65° C.
  5. stirringwith stirring
  6. extractionextracted three times with ethyl acetate
  7. extractionThen the combined organic phases are extracted three times with 10% aqueous sodium carbonate solution
  8. dry with materialThe organic phase is dried over magnesium sulphate

Sources & evidence

ORD record
ord-dee42749e3f548998fd43c6be0dcb245
Source dataset
uspto-grants-2008_05
Patent number
US07371753B2

Reaction notes

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