Water → HCID 13281441, compound

HRID 1763097Notes

Reaction equation

HRID 1763097 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-a9d20dbe3b3848f7b4813c205e118674
Source dataset
uspto-grants-1989_05
Patent number
US04835324

Reaction notes

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