반응 #450968

반응 방정식

4-fluoro-2-nitro-6-methylphenyl iodide

copper(I) cyanide

→

4-fluoro-2-nitro-6-methylbenzonitrile

수율 104.5%

용매

N,N-dimethylformamide

water

ethyl acetate

반응 조건

후처리

1. 1
   온도was heated at 150°-155° C. for 30 minutes
2. 2
   여과The mixture was filtered
3. 3
   기타the filtrate was placed in a separatory funnel
4. 4
   기타The organic layer was separated
5. 5
   세척the aqueous layer was washed with 200 mL of ethyl acetate
6. 6
   세척The combined wash
7. 7
   세척organic layer was then washed with three 150 mL portions of aqueous 5% lithium chloride
8. 8
   건조The mixture was dried with magnesium sulfate
9. 9
   여과filtered
10. 10
    농축The filtrate was concentrated under reduced pressure to a residue
11. 11
    세척Elution
12. 12
    농축concentrated under reduced pressure

실험 절차

A stirred mixture of 19.0 grams (0.068 mole) of 4-fluoro-2-nitro-6-methylphenyl iodide and 7.0 grams (0.078 mole) of copper(I) cyanide in 100 mL of N,N-dimethylformamide was heated at 150°-155° C. for 30 minutes. The reaction mixture was then diluted with 400 mL of water and 100 mL of ethyl acetate. The mixture was filtered, and the filtrate was placed in a separatory funnel. The organic layer was separated, and the aqueous layer was washed with 200 mL of ethyl acetate. The combined wash and organic layer was then washed with three 150 mL portions of aqueous 5% lithium chloride. The mixture was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 1:1 methylene chloride: petroleum ether. The product-containing fractions were combined and concentrated under reduced pressure, yielding 12.8 grams of 4-fluoro-2-nitro-6-methylbenzonitrile, mp 61°-63° C. The NMR spectrum was consistent with the proposed structure. Step E Synthesis of 2-amino-4-fluoro-6-methylbenzonitrile as an intermediate

출처