Water → β-Amino-3,4-difluorobenzeneethanol

HRID 278902

Reaction equation

HRID 278902 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][O:12]C(=O)[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].O.[OH-].[K+]>C(O)C>[NH2:10][CH:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)[CH2:13][OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 220487464-(3,4-Difluorophenyl)-1,3-oxazolidin-2-one

Product 1

HCID 22048878β-Amino-3,4-difluorobenzeneethanolYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (+)-4-(3,4-difluorophenyl)-oxazolidin-2-one (1.39 mmol, 0.27 g) in 5.0 mL ethanol was added 5.0 mL of water and pellets of potassium hydroxide (5.0 mmol, 0.28 g). The resulting solution was then heated to reflux overnight. The solvent was removed in vacuo and the resulting residue was extracted with EtOAc (2×50 mL). The organic extracts were washed with brine and the organic layer was dried over Na2SO4. It was filtered and the solvent was removed in vacuo to obtain (+)-2-amino-2-(3,4-difluorophenyl)-ethanol as a white solid (0.21 g, 87% yield).

Workup

  1. temperatureThe resulting solution was then heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed in vacuo
  4. extractionthe resulting residue was extracted with EtOAc (2×50 mL)
  5. washThe organic extracts were washed with brine
  6. dry with materialthe organic layer was dried over Na2SO4
  7. filtrationIt was filtered
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2e571f8b58f8487aaa9eeb32e8ab214e
Source dataset
uspto-grants-2002_03
Patent number
US06362182B1

Linked notes

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