Sodium Fluoride → HCID 11095876, compound

HRID 2166929Notes

Reaction equation

HRID 2166929 reaction equation
[C:1]1([CH2:7][C:8](=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:15]F.[F-].[Na+]>C(#N)C.ClC(Cl)(Cl)C(F)(F)F>[C:1]1([CH:7]([F:15])[C:8](=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 5235Sodium FluorideHCID 24524FluorineHCID 12292599Ethyl 2-oxo-3-phenylpropanoate

Product 1

HCID 11095876HCID 11095876, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 96351,1,1-Trichloro-2,2,2-trifluoroethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Ethyl 3-phenylpyruvate (10 g; 0.052 mol) is dissolved in a mixture of acetonitrile (60 g) and trichlorotrifluoroethane (410 g), and the resulting solution is cooled to -10° C. Then, fluorine gas (0.067 mol) diluted with nitrogen to 10% concentration is introduced therein over a period of 2.5 hours while stirring vigorously. After addition of sodium fluoride (2 g), the solvent is distilled off under reduced pressure, and the residue is rectified to give ethyl 3-phenyl-3-fluoropyruvate (4.37 g). Boiling point, 90°-95° C./1 mmHg.

Workup

  1. additionis introduced
  2. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-54f5c8e78f0d4be5a61589bfd83f751e
Source dataset
uspto-grants-1983_06
Patent number
US04390702

Reaction notes

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