반응 #80918

반응 방정식

2-amino-5-ethynyl-6-methylbenzonitrile

4-trifluoromethylphenyl iodide

triethylamine

→

2-amino-6-methyl-5-[(4-trifluoromethylphenyl)ethynyl]benzonitrile

수율 72.7%

용매

acetonitrile

반응 조건

후처리

1. 1
   농축After this time the reaction mixture was concentrated under reduced pressure to a residue
2. 2
   기타The residue was partitioned between ethyl acetate and aqueous 1N hydrochloric acid
3. 3
   여과The two-layered mixture was filtered
4. 4
   기타to remove a solid
5. 5
   기타The aqueous layer and the organic layer were separated
6. 6
   세척the aqueous layer was washed with ethyl acetate
7. 7
   세척The ethyl acetate wash
8. 8
   세척the combination was washed with an aqueous solution of 10% lithium chloride
9. 9
   건조The organic layer was dried with magnesium sulfate
10. 10
    여과filtered
11. 11
    농축The filtrate was concentrated under reduced pressure to a residue
12. 12
    기타The residue was triturated with methylene chloride
13. 13
    여과filtered
14. 14
    세척Elution
15. 15
    농축concentrated under reduced pressure

실험 절차

A solution of 3.5 grams (0.022 mole) of 2-amino-5-ethynyl-6-methylbenzonitrile, 8.4 grams (0.031 mole) of 4-trifluoromethylphenyl iodide, 10.7 grams (0.077 mole) of triethylamine, 0.5 gram (catalyst) of bis(triphenylphosphine)palladium(II) chloride, and 0.5 gram (catalyst) of copper(I) iodide in 100 mL of acetonitrile was stirred at ambient temperature for about 18 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was partitioned between ethyl acetate and aqueous 1N hydrochloric acid. The two-layered mixture was filtered to remove a solid. The aqueous layer and the organic layer were separated, and the aqueous layer was washed with ethyl acetate. The ethyl acetate wash was combined with the organic layer, and the combination was washed with an aqueous solution of 10% lithium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was triturated with methylene chloride and filtered. The filtrate was subjected to column chromatography on silica gel. Elution was accomplished using methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 4.8 grams of 2-amino-6-methyl-5-[(4-trifluoromethylphenyl)ethynyl]benzonitrile, mp 136°-138° C. The NMR spectrum was consistent with the proposed structure.

출처