Potassium Carbonate → HCID 68748803, compound

HRID 1963768Notes

Reaction equation

HRID 1963768 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH:21]=[CH2:22]>C(#N)C>[CH2:22]([O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1)[CH2:21][CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21241Homoallyl bromideHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 68748803HCID 68748803, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile (25 mL) solution of 3-fluoro-4-nitrophenol (1.57 g; 10.0 mmol) and potassium carbonate (2.09 g; 15.1 mmol), 4-bromo-1-butene (2.21 g; 16.0 mmol) was added, and the mixture was refluxed and then reacted overnight. After completion of the reaction, the solution was filtrated by Celite, and then the filtrate was concentrated under a reduced pressure. The residue was purified by column chromatography (solvent, hexane:methylene chloride=6:4) using methylene chloride, and then the effluent was concentrated to obtain 4-(3-butenyloxy)-2-fluoronitrobenzene (1g) (1.71 g, 81% of yield, a light yellow oil) represented by the following formula.

Workup

  1. temperaturethe mixture was refluxed
  2. customreacted overnight
  3. customAfter completion of the reaction
  4. filtrationthe solution was filtrated by Celite
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. customThe residue was purified by column chromatography (solvent, hexane:methylene chloride=6:4)
  7. concentrationthe effluent was concentrated

Sources & evidence

ORD record
ord-a224ae7f696d4eb6a4f21ba8b7d8ec02
Source dataset
uspto-grants-2013_04
Patent number
US08415451B2

Reaction notes

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