Water → HCID 19068766, compound

HRID 1957264Notes

Reaction equation

HRID 1957264 reaction equation
B1([O-])OO1.[OH2:5].O.O.O.[Na+].[Cl:10][C:11]1[C:12]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH:28]=[O:29])[CH:22]=2)=[N:13][CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1.O>C(O)(=O)C>[Cl:10][C:11]1[C:12]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([OH:5])=[O:29])[CH:22]=2)=[N:13][CH:14]=[C:15]([C:17]([F:20])([F:18])[F:19])[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 186929322-Chloro-5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]benzaldehydeHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 19068766HCID 19068766, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

38.5 g of sodium perborate tetrahydrate were added in portions over the course of 30 minutes to a solution of 16.0 g of 3-chloro-2-(4-chloro-3-formylphenyl)-5-trifluoromethylpyridine in 100 ml of glacial acetic acid at 100° C., followed by stirring at 100° C. for 1.5 hours. The mixture was cooled and then poured into 400 ml of water. The product was extracted from the aqueous phase with 3×100 ml of tert-butyl methyl ether. The combined organic phases were dried over sodium sulfate and then concentrated. The residue was triturated with n-hexane. The material insoluble in hexane was removed and extracted by boiling twice with ether, the pyridine N-oxide byproduct remaining undissolved. The combined ether phases were dried over sodium sulfate and concentrated to result in 13.7 g (81%) of colorless crystals; melting point: 149°-151° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe product was extracted from the aqueous phase with 3×100 ml of tert-butyl methyl ether
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was triturated with n-hexane
  6. customThe material insoluble in hexane was removed
  7. extractionextracted
  8. dry with materialThe combined ether phases were dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4817f538a9ba412ca9a8994d2537bb13
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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