반응 #41509

반응 방정식

2-Bromo-4-methylphenol

Potassium fluoride

CH2Cl2

Trimethylsilylacetylene

→

2-ethynyl-4-methyl-phenol

용매

Et3N dioxane

반응 조건

후처리

1. 1
   기타A flask is flushed with N2
2. 2
   기타The solvents are removed under vacuum
3. 3
   추출the resulting liquid is extracted
4. 4
   세척by washing with ethyl ether
5. 5
   세척washed with H2O
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   기타The solvent was removed under vacuum
8. 8
   기타the product is purified by column chromatography
9. 9
   기타flushed flask
10. 10
    workup.DISSOLUTIONdissolved in methanol
11. 11
    workup.STIRRINGthe reaction stirred under a N2 blanket for 16 h
12. 12
    추출extracted with H2O
13. 13
    건조dried over Na2SO4
14. 14
    여과filtered
15. 15
    기타the solvent is removed under vacuum
16. 16
    기타The resulting product is purified by column chromatography

실험 절차

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).

출처