5-Fluoro-2-iodo-3-nitrotoluene → 4-Fluoro-2-methyl-6-nitrobenzonitrile

HRID 17548

반응식

HRID 17548 반응식
[Cu](C#N)[C:2]#[N:3].[F:6][C:7]1[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[C:10](I)=[C:11]([CH3:13])[CH:12]=1>CN(C)C=O>[F:6][C:7]1[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[C:10]([C:2]#[N:3])=[C:11]([CH3:13])[CH:12]=1

참가 물질

4

반응물 2

HCID 541243255-Fluoro-2-iodo-3-nitrotolueneHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 544206034-Fluoro-2-methyl-6-nitrobenzonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

Copper cyanide (11.9 g, 133 mmol) was added to an N,N-dimethylformamide (240 ml) solution of 5-fluoro-2-iodo-1-methyl-3-nitrobenzene (I-262) (34.0 g, crude product), followed by heating at 130° C. for 3.5 hours. After cooling, the insoluble matter was removed by filtration under suction, water was added to the filtrate, and the precipitated insoluble matter was removed by filtration through Celite under suction. The filtrate was extracted with ethyl acetate, the organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, then the residue was subjected to column chromatography, and eluted with a mixed solvent of n-hexane/ethyl acetate (3:1, v/v) to obtain the entitled compound (17.6 g, 81% from I-235) as a red brown solid.

후처리

  1. temperatureAfter cooling
  2. customthe insoluble matter was removed by filtration under suction, water
  3. additionwas added to the filtrate
  4. customthe precipitated insoluble matter was removed by filtration through Celite under suction
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated away under reduced pressure
  9. washeluted with a mixed solvent of n-hexane/ethyl acetate (3:1
  10. customv/v) to obtain the entitled compound (17.6 g, 81% from I-235) as a red brown solid

출처 및 근거

ORD 기록
ord-eab29c0e19dd4feaad09e1dc1511bf3b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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