5-Fluoro-2-nitrophenol → 2-(Benzyloxy)-4-fluoro-1-nitrobenzene

HRID 1496953Notes

Reaction equation

HRID 1496953 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[CH2:12](I)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium CarbonateHCID 12098Benzyl iodide

Product 1

HCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-fluoro-2-nitrophenol (300 mg), benzyl iodide (0.50 mL) and potassium carbonate (500 mg) were dissolved in dimethylformamide (DMF, 3 mL) and reacted at 50° C. overnight. The dimethylformamide of the reaction mixture was concentrated under reduced pressure, added with water and the organic layer was extracted with ethyl acetate. The organic layer was washed with brine, and the water was removed with sodium sulfate, and the solvent was removed under reduced pressure. The thus obtained compound was used in the subsequent reaction without further purification.

Workup

  1. customreacted at 50° C. overnight
  2. concentrationThe dimethylformamide of the reaction mixture was concentrated under reduced pressure
  3. additionadded with water
  4. extractionthe organic layer was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customthe water was removed with sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe thus obtained compound was used in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-e3e93ea8b3004803beb6b64920441599
Source dataset
uspto-grants-2015_12
Patent number
US09199944B2

Reaction notes

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