Reacción #41509

Ecuación de reacción

2-Bromo-4-methylphenol

Potassium fluoride

CH2Cl2

Trimethylsilylacetylene

→

2-ethynyl-4-methyl-phenol

Disolventes

Et3N dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA flask is flushed with N2
2. 2
   OtroThe solvents are removed under vacuum
3. 3
   Extracciónthe resulting liquid is extracted
4. 4
   Lavadoby washing with ethyl ether
5. 5
   Lavadowashed with H2O
6. 6
   Secadodried over anhydrous sodium sulfate
7. 7
   OtroThe solvent was removed under vacuum
8. 8
   Otrothe product is purified by column chromatography
9. 9
   Otroflushed flask
10. 10
    workup.DISSOLUTIONdissolved in methanol
11. 11
    workup.STIRRINGthe reaction stirred under a N2 blanket for 16 h
12. 12
    Extracciónextracted with H2O
13. 13
    Secadodried over Na2SO4
14. 14
    Filtraciónfiltered
15. 15
    Otrothe solvent is removed under vacuum
16. 16
    OtroThe resulting product is purified by column chromatography

Procedimiento

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).

Fuente