反应详情

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).

1. customA flask is flushed with N2
2. customThe solvents are removed under vacuum
3. extractionthe resulting liquid is extracted
4. washby washing with ethyl ether
5. washwashed with H2O
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was removed under vacuum
8. customthe product is purified by column chromatography
9. customflushed flask
10. dissolutiondissolved in methanol
11. stirringthe reaction stirred under a N2 blanket for 16 h
12. extractionextracted with H2O
13. dry with materialdried over Na2SO4
14. filtrationfiltered
15. customthe solvent is removed under vacuum
16. customThe resulting product is purified by column chromatography