Water → HCID 13281441, compound

HRID 648815Notes

Reaction equation

HRID 648815 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]#[CH:21].O>C(#N)C>[Cl:1][C:2]1[C:3]([O:12][CH2:21][C:20]#[CH:19])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-

Product 1

HCID 13281441HCID 13281441, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-4-fluoro-5-nitrophenol (19.1 g) in acetonitrile (100 ml), there was added anhydrous potassium carbonate (8 g). After stirring at room temperature for several minutes, propargyl bromide (14 g) was added thereto, and the resultant mixture was heated under reflux for 3 hours. After being allowed to cool to room temperature, water was added thereto, and the reaction mixture was extracted with ether. The ether extract was washed with a 5% aqueous sodium hydroxide solution and water in this order, dried over anhydrous magnesium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethanol to obtain 13.5 g of 4-chloro-2-fluoro-5-(2-propynyloxy)nitrobenzene. M.P. 88°-89° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureto cool to room temperature
  3. extractionthe reaction mixture was extracted with ether
  4. extractionThe ether extract
  5. washwas washed with a 5% aqueous sodium hydroxide solution and water in this order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationsubjected to filtration
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-657fa056a27645758ac8cb4540b83a89
Source dataset
uspto-grants-1988_04
Patent number
US04736068

Reaction notes

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