5-Fluoro-2-nitrophenol → HCID 86747314, compound

HRID 1376714Notes

Reaction equation

HRID 1376714 reaction equation
CN1[C:6](=[O:7])[CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[F:14][C:15]1[CH:16]=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[C:19](O)[CH:20]=1.BrCCC=C>O.CC(C)=O>[CH:6]([O:7][C:20]1[CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=[CH:16][C:15]=1[F:14])=[CH:5][CH2:4][CH3:3]

Participants

7

Reactant 4

HCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 21241Homoallyl bromide

Product 1

HCID 86747314HCID 86747314, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a suspension of NMP (20 ml), acetone (20 ml) and potassium carbonate (8.85 g) was added 5-fluoro-2-nitro phenol (5.0 g, 30 mmol) in one portion. After 15 minutes, the suspension began to turn yellow. After stirring 30 minutes under nitrogen, 4-bromobutene (4.25 ml) was added and the suspension was refluxed for 18 hours. The suspension was poured into water and extracted with 3×200 ml of diethyl ether. The aqueous layer was acidified with 2N HCl and extracted with ether. The ether layers were combined, washed with 2N HCl and water and dried over anhydrous magnesium sulfate. Filtration and in vacuo concentration yielded 6.0 g of 2-(3-butenyloxy-4-fluoronitrobenzene, as an oil, which was used in the next step without further purification.

Workup

  1. temperaturethe suspension was refluxed for 18 hours
  2. extractionextracted with 3×200 ml of diethyl ether
  3. extractionextracted with ether
  4. washwashed with 2N HCl and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration
  7. concentrationin vacuo concentration

Sources & evidence

ORD record
ord-58d76ca8afe84eae8d4112b0dfdab9af
Source dataset
uspto-grants-1997_09
Patent number
US05663308

Reaction notes

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