Citric Acid → HCID 178469642, compound

HRID 2404578Notes

Reaction equation

HRID 2404578 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:25]CC)=[N:8][N:9]([C:11]2[CH:16]=[C:15]([S:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([CH3:23])=[CH:13][C:12]=2[F:24])[CH:10]=1)=[O:5])[CH3:2].B(Br)(Br)Br.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:25])=[N:8][N:9]([C:11]2[CH:16]=[C:15]([S:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([CH3:23])=[CH:13][C:12]=2[F:24])[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 25134Boron tribromideHCID 68480474HCID 68480474, compound

Product 1

HCID 178469642HCID 178469642, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Then, 1.0 g of ethyl-3-ethoxy-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}pyrazole-4-carboxylate was dissolved in 30 mL of dichloromethane, and 3.08 g of boron tribromide was added under cooling with ice, followed by stirring at room temperature for 12 hours. Then, 10 mL of a saturated aqueous solution of citric acid was added, extraction with ethyl acetate was carried out, the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:1) to obtain 0.45 g of ethyl-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-hydroxypyrazole-4-carboxylate.

Workup

  1. temperatureunder cooling with ice
  2. extractionextraction with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-3736409e15de4c84bba1748821b5a0f8
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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