Potassium Hydroxide → 2,3,5,6-Tetrafluoro-4-nitrophenol

HRID 1870622Notes

Reaction equation

HRID 1870622 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([F:11])[C:5]([F:12])=[C:4](F)[C:3]=1[F:14].[OH-:15].[K+]>CS(C)=O.O>[N+:8]([C:7]1[C:2]([F:1])=[C:3]([F:14])[C:4]([OH:15])=[C:5]([F:12])[C:6]=1[F:11])([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 70154Pentafluoronitrobenzene

Product 1

HCID 6110932,3,5,6-Tetrafluoro-4-nitrophenolYield 95%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

21.3 g of pentafluoronitrobenzene (0.1 mol) are dissolved in 400 ml of dimethyl sulfoxide; a solution of 11.2 g of potassium hydroxide (0.2 mol) in 100 ml of water is added drop wise to this solution with vigorous stirring. After 24 hours at room temperature, the crude product is washed by shaking with 200 ml of ethyl acetate and 400 ml of water. The organic phase is washed three times with water, dried over sodium sulfate and evaporated to half in a rotary evaporator. The reaction product is then recrystallized from a mixture of ethyl acetate and n-hexane (volume ratio 1:1) and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (yield: 95%).

Workup

  1. washthe crude product is washed
  2. washThe organic phase is washed three times with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to half in a rotary evaporator
  5. customThe reaction product is then recrystallized from a mixture of ethyl acetate and n-hexane (volume ratio 1:1)
  6. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  7. customdrying cabinet (yield: 95%)

Sources & evidence

ORD record
ord-8089e53ca7a846a6b49836ea36a61f49
Source dataset
uspto-grants-2000_08
Patent number
US06096921

Reaction notes

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