Reaktion #41509

Reaktionsgleichung

2-Bromo-4-methylphenol

Potassium fluoride

CH2Cl2

Trimethylsilylacetylene

→

2-ethynyl-4-methyl-phenol

Lösungsmittel

Et3N dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA flask is flushed with N2
2. 2
   SonstigeThe solvents are removed under vacuum
3. 3
   Extraktionthe resulting liquid is extracted
4. 4
   Waschenby washing with ethyl ether
5. 5
   Waschenwashed with H2O
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   SonstigeThe solvent was removed under vacuum
8. 8
   Sonstigethe product is purified by column chromatography
9. 9
   Sonstigeflushed flask
10. 10
    workup.DISSOLUTIONdissolved in methanol
11. 11
    workup.STIRRINGthe reaction stirred under a N2 blanket for 16 h
12. 12
    Extraktionextracted with H2O
13. 13
    Trocknendried over Na2SO4
14. 14
    Filtrationfiltered
15. 15
    Sonstigethe solvent is removed under vacuum
16. 16
    SonstigeThe resulting product is purified by column chromatography

Vorschrift

A flask is flushed with N2 and charged with 2-Bromo-4-methylphenol (20 mmol) and dissolved in 1/1 Et3N/dioxane. Bis(triphenylphosphine)palladium(II) dichloride (PdCl2(PPh3)2) (0.2 mmol) is added, followed by 0.4 mmol of CuI. Trimethylsilylacetylene (24 mmol) is added drop-wise to the reaction mixture. The reaction mixture is stirred overnight under N2. The solvents are removed under vacuum and the resulting liquid is extracted by washing with ethyl ether. The ethyl ether extracts are combined and washed with H2O, then dried over anhydrous sodium sulfate. The solvent was removed under vacuum and the product is purified by column chromatography. The purified product is placed in a N2-flushed flask and dissolved in methanol. Potassium fluoride (65 mmol) is added and the reaction stirred under a N2 blanket for 16 h. The reaction mixture is poured into CH2Cl2 and extracted with H2O, then dried over Na2SO4, filtered and the solvent is removed under vacuum. The resulting product is purified by column chromatography to yield 2-ethynyl-4-methyl-phenol (3).

Quelle