Dimethyl Sulfoxide → 5-Fluoro-2-nitroanisole

HRID 349135Notes

Reaction equation

HRID 349135 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.[CH3:12]S(C)=O.CI.[OH-].[K+]>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 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodide2×HCID 99375-Fluoro-2-nitrophenolHCID 14797Potassium Hydroxide

Product 1

HCID 27792505-Fluoro-2-nitroanisole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

25 g (0.159 mol) of 5-fluoro-2-nitrophenol are added to 125 ml of DMSO. 22.5 g (0.159 mol) of methyl iodide are then added, followed by dropwise addition, while keeping the temperature below 25° C., of 17.8 g of aqueous 50% potassium hydroxide solution. The mixture is stirred for one hour at ambient temperature and a further 22.5 g (0.159 mol) of methyl iodide are then added. After stirring for 24 hours, the reaction medium is poured into 125 ml of water and then extracted with 60 ml of dichloromethane. The organic phase is washed with 90 ml of aqueous sodium hydroxide solution (1N) and then with 60 ml of water. After drying over MgSO4, the organic phase is concentrated under reduced pressure. 20.59 g (76%) of 4-fluoro-2-methoxy-1-nitrobenzene (1) are thus recovered.

Workup

  1. additionfollowed by dropwise addition
  2. customthe temperature below 25° C.
  3. stirringAfter stirring for 24 hours
  4. extractionextracted with 60 ml of dichloromethane
  5. washThe organic phase is washed with 90 ml of aqueous sodium hydroxide solution (1N)
  6. dry with materialAfter drying over MgSO4
  7. concentrationthe organic phase is concentrated under reduced pressure
  8. custom20.59 g (76%) of 4-fluoro-2-methoxy-1-nitrobenzene (1) are thus recovered

Sources & evidence

ORD record
ord-6f0592e3e00049b18f78dc1498311dcc
Source dataset
uspto-grants-2007_02
Patent number
US07179301B2

Reaction notes

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