Water → 5-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid

HRID 2069256Notes

Reaction equation

HRID 2069256 reaction equation
ClC(Cl)(Cl)Cl.C(#N)C.[F:9][C:10]1[CH:15]=[C:14]([C:16](Cl)=C(Cl)Cl)[C:13]([N+:21]([O-:23])=[O:22])=[CH:12][C:11]=1[C:24]([F:27])([F:26])[F:25].I([O-])(=O)(=O)=[O:29].[Na+].[OH2:34]>O.[Ru](Cl)(Cl)Cl>[F:9][C:10]1[C:11]([C:24]([F:27])([F:26])[F:25])=[CH:12][C:13]([N+:21]([O-:23])=[O:22])=[C:14]([CH:15]=1)[C:16]([OH:29])=[O:34]

Participants

7

Reactant 5

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 6342AcetonitrileHCID 23667635Sodium periodate2×HCID 589645301-Fluoro-4-nitro-5-trichlorovinyl-2-trifluoromethyl-benzene

Product 1

HCID 589645095-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 6093376Ruthenium trichloride hydrateCatalyst2×

Conditions

Temperature
60 °C

Procedure

To 300 ml of a solvent mixture of tetrachloromethane, acetonitril and water (10:10:15) are added sequentially 8.5 g (25 mmole) of 1-fluoro-4-nitro-5-trichlorovinyl-2-trifluoromethyl-benzene, 1 g (8 mol%) of ruthenium trichloride monohydrate and 23 g (0.1 mole) of sodium periodate. After stirring at 60° C. for 16 hours additional 1 g of ruthenium trichloride monohydrate and 23 g of sodium periodate are added and stirring at 60° C. is continued for 4 hours. The cooled reaction is filtered over Celite and the filtrate evaporated to dryness. 150 ml of a 1M sodium hydroxide solution are added and extracted two times with 150 ml of dichloro-methane. The aqueous phase is acidified with concentrated hydrochloric acid and extracted four times with 100 ml dichloro-methane. The combined organic phases are dried over sodium sulfate, filtered and evaporated. The residue is recrystallized from acetone/petrolether to give 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid of m.p. 142-145° C.

Workup

  1. additionare added
  2. customThe cooled reaction
  3. filtrationis filtered over Celite
  4. customthe filtrate evaporated to dryness
  5. addition150 ml of a 1M sodium hydroxide solution are added
  6. extractionextracted two times with 150 ml of dichloro-methane
  7. extractionextracted four times with 100 ml dichloro-methane
  8. dry with materialThe combined organic phases are dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is recrystallized from acetone/petrolether

Sources & evidence

ORD record
ord-68d99b4ae06b4a4483770f55cb21d055
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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