Hydrochloric Acid → 3,5-Difluoro-2-nitrophenol

HRID 1372563Notes

Reaction equation

HRID 1372563 reaction equation
CS(C)=O.[OH-:5].[Na+].[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10](F)[C:9]=1[N+:16]([O-:18])=[O:17].Cl>CCOCC.O>[F:7][C:8]1[C:9]([N+:16]([O-:18])=[O:17])=[C:10]([OH:5])[CH:11]=[C:12]([F:14])[CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl Sulfoxide2×HCID 14798Sodium HydroxideHCID 675671,3,5-Trifluoro-2-nitrobenzene

Product 1

HCID 118195353,5-Difluoro-2-nitrophenolYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Dimethylsulfoxide (which will hereinafter be abbreviated as “DMSO”) (50 ml) and 10N NaOH (12 ml, 120 mmol) were added to 1,3,5-trifluoro-2-nitrobenzene (10.0 g, 56.5 mmol). The mixture was stirred at room temperature for 15 hours. Water (100 ml) and ether (200 ml) were added to separate the reaction mixture into layers. The water layer thus obtained was acidified with 1N HCl, followed by extraction with ether (2×200 ml). The extract was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (10:1) eluate fractions, the title compound (7.97 g, 81%) was obtained as a yellow crystalline powder.

Workup

  1. customto separate the reaction mixture into layers
  2. customThe water layer thus obtained
  3. extractionfollowed by extraction with ether (2×200 ml)
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (10:1) eluate fractions

Sources & evidence

ORD record
ord-1de5f60ec9f647d7a02dc3ccfab5ed68
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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