Ammonia → 5-Amino-2,4-difluorophenol

HRID 634671Notes

Reaction equation

HRID 634671 reaction equation
N.[F:2][C:3]1[CH:9]=[C:8]([F:10])[C:7]([O:11]C(OC)=O)=[CH:6][C:4]=1[NH2:5]>C(O)C.O>[F:2][C:3]1[CH:9]=[C:8]([F:10])[C:7]([OH:11])=[CH:6][C:4]=1[NH2:5]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 21260327HCID 21260327, compound

Product 1

HCID 27829995-Amino-2,4-difluorophenolYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Concentrated aqueous ammonia (20 ml) was added to a solution of 2,4-difluoro-5-methoxycarbonyloxyaniline (2.0 g, 9.85 mmol) in ethanol (100 ml) and the mixture stirred at ambient temperature for 3 hours. The reaction mixture was diluted with water and most of the organic volatiles were removed by evaporation. The aqueous residue was neutralised to pH7 and extracted with ethyl acetate. The extracts were washed with water, dried (MgSO4) and the solvent removed by evaporation to give 2,4-difluoro-5-hydroxyaniline (1.2 g, 85%).

Workup

  1. customwere removed by evaporation
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-34648b17e061425b8c14f53d75ba76db
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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