Fluorine → HCID 10584032, compound

HRID 2166930Notes

Reaction equation

HRID 2166930 reaction equation
[C:1]1([CH2:7][C:8](=[O:13])[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:14]F>C(#N)C.ClC(Cl)(Cl)C(F)(F)F>[C:1]1([CH:7]([F:14])[C:8](=[O:13])[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 24524FluorineHCID 562359Methyl 2-oxo-3-phenylpropanoate

Product 1

HCID 10584032HCID 10584032, compound

Reagents, catalysts & solvents 2

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

Procedure

In the same manner as in Example 1, methyl 3-phenylpyruvate (35.62 g; 0.2 mol) is dissolved in a mixture of acetonitrile (240 g) and trichlorotrifluoroethane (1.6 L) and reacted with fluorine at -10° C. After the same work-up as in Example 1, the residue is rectified to give methyl 3-phenyl-3-fluoropyruvate (11.8 g). The silyl enol ether obtained by the treatment of the above product with bis-(trimethylsilyl)acetamide (BSA) in methylene chloride shows boiling point 93°-95° C./1 mmHg and 19F NMR (CDCl3), δ (int. C6F6)+31.5 (s).

Sources & evidence

ORD record
ord-54f2d6e835cd406fb374fd17d142a38c
Source dataset
uspto-grants-1983_06
Patent number
US04390702

Reaction notes

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