Potassium Carbonate → 2-Fluoro-6-nitrophenyl Trifluoromethanesulfonate

HRID 1722451Notes

Reaction equation

HRID 1722451 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]([F:25])([F:24])[S:20](Cl)(=[O:22])=[O:21]>CC(C)=O>[F:18][C:19]([F:25])([F:24])[S:20]([O:11][C:3]1[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 737102-Fluoro-6-nitrophenolHCID 79000Trifluoromethanesulfonyl chloride

Product 1

HCID 200290852-Fluoro-6-nitrophenyl TrifluoromethanesulfonateYield 53.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture consisting of 2-fluoro-6-nitrophenol (20 g, 0.14 mol) and potassium carbonate (20 g, 0.14 mol) in acetone (350 mL) was stirred at room temperature for 20 minutes. A solution of trifluoromethanesulfonyl chloride (23.7 g, 0.14 mol) in acetone (100 mL) was added dropwise at room temperature. Stirring was continued for 3 hours. The reaction was filtered, and the filtrate was concentrated. The residue was dissolved in diethyl ether (300 mL), washed with 0.1N NaOH, water, dried (MgSO4), filtered and evaporated to give 21.5 g of the title compound.

Workup

  1. stirringStirring
  2. waitwas continued for 3 hours
  3. filtrationThe reaction was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in diethyl ether (300 mL)
  6. washwashed with 0.1N NaOH, water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-a4f64d8ef6da4e7ba3212b0094efb4af
Source dataset
uspto-grants-1989_08
Patent number
US04855445

Reaction notes

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