Hydrochloric Acid → HCID 15818877, compound

HRID 1736239Notes

Reaction equation

HRID 1736239 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.[C:11](Cl)(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].Cl>N1C=CC=CC=1>[F:9][C:5]1[CH:4]=[C:3]([F:10])[C:2]([NH:1][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][C:6]=1[OH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 62493Pivaloyl chlorideHCID 27829995-Amino-2,4-difluorophenol

Product 1

HCID 15818877HCID 15818877, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

18.9 g (130 mmol) of the resulting 5-amino-2,4-difluorophenol was dissolved in 45 ml of pyridine, 16.0 ml of pivaloyl chloride was added dropwise over 8 minutes under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. 1N hydrochloric acid was added to the reaction solution and the mixture was extracted with ether. The organic layer was washed once with a 1N aqueous solution of hydrochloric acid, water and an aqueous saturated solution of sodium chloride, respectively, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was triturated with n-hexane to give 27.0 g (91%) of 2,4-difluoro-5-pivaloylaminophenol.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ether
  3. washThe organic layer was washed once with a 1N aqueous solution of hydrochloric acid, water
  4. dry with materialan aqueous saturated solution of sodium chloride, respectively, and dried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-9714afc0c76445c5a919769c2fe63740
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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