Sodium Hydroxide → 3,5-Difluoro-2-nitrophenol

HRID 2305632Notes

Reaction equation

HRID 2305632 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4](F)[C:3]=1[N+:10]([O-:12])=[O:11].[OH-:13].[Na+]>CS(C)=O.O>[F:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([OH:13])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 675671,3,5-Trifluoro-2-nitrobenzene

Product 1

HCID 118195353,5-Difluoro-2-nitrophenol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 2,4,6-trifluoronitrobenzene (10 g) in dimethyl sulphoxide(50 mL) was treated with 10N sodium hydroxide(12 mL) and the mixture was stirred at room temperature for 18 h. The mixture was diluted with water and washed with ether. The aqueous phase was then acidified and extracted with ether. The extract was washed with brine, dried and evaporated to dryness and the residue was purified by flash chromatography eluting with increasingly polar mixtures of ethyl acetate and hexane to give the product(8.3 g) [m/e 174, MH−].

Workup

  1. washwashed with ether
  2. extractionextracted with ether
  3. washThe extract was washed with brine
  4. customdried
  5. customevaporated to dryness
  6. customthe residue was purified by flash chromatography
  7. washeluting
  8. temperaturewith increasingly polar mixtures of ethyl acetate and hexane

Sources & evidence

ORD record
ord-3b5114d4eec04139822a63e2aa3720cb
Source dataset
uspto-grants-2002_08
Patent number
US06441012B1

Reaction notes

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