Hydrochloric Acid → 2,3-Difluoro-6-nitrophenol

HRID 851077Notes

Reaction equation

HRID 851077 reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[OH-:13].[K+].Cl>CS(C)=O.O.C(Cl)(Cl)Cl>[F:8][C:7]1[C:6]([F:9])=[CH:5][CH:4]=[C:3]([N+:10]([O-:12])=[O:11])[C:2]=1[OH:13]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 698711,2,3-Trifluoro-4-nitrobenzene

Product 1

HCID 27337452,3-Difluoro-6-nitrophenol

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

20 g of 2,3,4-trifluoronitrobenzene was dissolved in 150 ml of dimethyl sulfoxide, and to this mixture a solution of 10% potassium hydroxide was added dropwise while keeping the temperature at 18° to 20° C. Then, the mixture was stirred for 2 hours at room temperature and one liter of water was added to this reaction mixture and the mixture was shaken with chloroform. The water layer was acidified with hydrochloric acid and was extracted with chloroform. The extract was washed with water and was dried, then chloroform layer was concentrated. The residue was purified by silica gel column chromatography to provide 5.8 g of 2,3-difluoro-6-nitrophenol as yellow oil.

Workup

  1. customat 18° to 20° C
  2. extractionwas extracted with chloroform
  3. washThe extract was washed with water
  4. customwas dried
  5. concentrationchloroform layer was concentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4cb9cd969220439ab76eb934f811de98
Source dataset
uspto-grants-1983_05
Patent number
US04382892

Reaction notes

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