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

HRID 17548笔记

反应方程式

HRID 17548 反应方程式
[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

参与物

4

反应物 2

HCID 541243255-Fluoro-2-iodo-3-nitrotolueneHCID 178418260HCID 178418260，化合物

产物 1

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

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
130 °C

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-eab29c0e19dd4feaad09e1dc1511bf3b
来源数据集
uspto-grants-2010_06
专利号
US07737166B2

反应笔记

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