反应 #80918

反应方程式

2-amino-5-ethynyl-6-methylbenzonitrile

4-trifluoromethylphenyl iodide

triethylamine

→

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

收率 72.7%

溶剂

acetonitrile

反应条件

后处理

1. 1
   浓缩After this time the reaction mixture was concentrated under reduced pressure to a residue
2. 2
   其他The residue was partitioned between ethyl acetate and aqueous 1N hydrochloric acid
3. 3
   过滤The two-layered mixture was filtered
4. 4
   其他to remove a solid
5. 5
   其他The aqueous layer and the organic layer were separated
6. 6
   洗涤the aqueous layer was washed with ethyl acetate
7. 7
   洗涤The ethyl acetate wash
8. 8
   洗涤the combination was washed with an aqueous solution of 10% lithium chloride
9. 9
   干燥The organic layer was dried with magnesium sulfate
10. 10
    过滤filtered
11. 11
    浓缩The filtrate was concentrated under reduced pressure to a residue
12. 12
    其他The residue was triturated with methylene chloride
13. 13
    过滤filtered
14. 14
    洗涤Elution
15. 15
    浓缩concentrated under reduced pressure

实验过程

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.

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