5-Fluoro-2-nitrophenol → 4-Fluoro-1-nitro-2-propoxybenzene

HRID 1496947Notes

Reaction equation

HRID 1496947 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)[CH2:13][CH3:14].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][CH2:13][CH3:14])[CH:7]=1

Participants

5

Reactant 3

HCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium CarbonateHCID 336431-Iodopropane

Product 1

HCID 547587664-Fluoro-1-nitro-2-propoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-fluoro-2-nitrophenol (300 mg), n-propyl 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-01896cb76259440ea4add1498a4a2a01
Source dataset
uspto-grants-2015_12
Patent number
US09199944B2

Reaction notes

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