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

HRID 486970Notes

Reaction equation

HRID 486970 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-].[K+].S(=O)(=O)(O)[OH:16]>O>[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:16]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 698711,2,3-Trifluoro-4-nitrobenzene

Product 1

HCID 27337452,3-Difluoro-6-nitrophenolYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

1.77 kg (10 mol) of 2,3,4-trifluoronitrobenzene are added to 4 l of water. The mixture is then warmed to 40° C. and vigorously stirred. 389.4 g (22 mol) of 31.7% strength potassium hydroxide solution are then added dropwise in such a way that the temperature remains between 40° and 55° C. After about 4 h, the reaction is complete (GC checking). The reaction mixture is brought to pH 3 using 70% strength sulfuric acid at 70° C. Steam is then passed into the solution, the product passing over with it and being isolated after cooling to 10° C. 1.51 kg of 2,3-difluoro-6-nitrophenol having a purity >99.9% (GC) are obtained after drying (melting point 63.5° C.), which corresponds to a yield of 86% of theory.

Workup

  1. customremains between 40° and 55° C
  2. customat 70° C
  3. custombeing isolated
  4. temperatureafter cooling to 10° C

Sources & evidence

ORD record
ord-ddd90a9de4b74431b89d63ffa2e0de5e
Source dataset
uspto-grants-1994_03
Patent number
US05292967

Reaction notes

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