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

HRID 1451685Notes

Reaction equation

HRID 1451685 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 2 N HCl and extracted with ether. The ether layers were combined, washed with 2 N 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 2 N HCl and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration
  7. concentrationin vacuo concentration

Sources & evidence

ORD record
ord-60742bb09d3e4a859ed5e5c4a9b41712
Source dataset
uspto-grants-1997_02
Patent number
US05605726

Reaction notes

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