Trifluoroacetic acid → HCID 23284769, compound

HRID 369204Notes

Reaction equation

HRID 369204 reaction equation
FC(F)(F)C(O)=O.B1([O-])OO1.[OH2:12].[OH2:13].O.O.[Na+].[NH2:17][C:18]1[C:27]([F:28])=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([F:29])[C:19]=1[CH3:30]>C(O)(=O)C>[F:29][C:20]1[C:19]([CH3:30])=[C:18]([N+:17]([O-:13])=[O:12])[C:27]([F:28])=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 23284817HCID 23284817, compoundHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 23284769HCID 23284769, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Trifluoroacetic acid (50 ml), acetic acid (50 ml) and sodium perborate tetrahydrate (26.6 g) were added to methyl 4-amino-2,5-difluoro-3-methylbenzoate (7.5 g), and the mixture was stirred at 60° C. for 24 hours. Impurities in the reaction mixture was removed by filtration, chloroform was added to the resultant filtrate, and the resultant mixture was washed with water. After an organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain the title compound (6.1 g) as a reddish brown oil.

Workup

  1. customImpurities in the reaction mixture was removed by filtration, chloroform
  2. additionwas added to the resultant filtrate
  3. washthe resultant mixture was washed with water
  4. dry with materialAfter an organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-640b430be87744faa8ebd98047b8cc25
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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