Ammonium Hydroxide → 2,3-Difluoro-5-nitrophenol

HRID 1803151Notes

Reaction equation

HRID 1803151 reaction equation
[OH-].[NH4+].C(=O)(OCC)[O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([F:14])[C:6]=1[F:15]>CCOC(C)=O>[F:15][C:6]1[C:7]([F:14])=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=1[OH:4]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 66859069HCID 66859069, compound

Product 1

HCID 221546562,3-Difluoro-5-nitrophenolYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Step M (3): Aqueous ammonium hydroxide (5 mL) was added to a solution of 2,3-difluoro-5-nitrophenyl ethyl carbonate (250 mg, 1.0 mol) in EtOAc (4 mL). The reaction mixture was quenched with 1 N HCl. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2,3-difluoro-5-nitrophenol (150 mg, 85% yield).

Workup

  1. customThe reaction mixture was quenched with 1 N HCl
  2. additionThe mixture was diluted with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-960946d47f3c4bf8978c4a0ab66f48b5
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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