Acetic Anhydride → 4-Bromo-5-nitrothiophene-2-carbonitrile

HRID 132075ノート

反応式

HRID 132075 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[N:11]O)[S:5][C:6]=1[N+:7]([O-:9])=[O:8].C(OC(=O)C)(=O)C>CCCCCCC.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:10]#[N:11])[S:5][C:6]=1[N+:7]([O-:9])=[O:8]

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 738521524-Bromo-5-nitro-thiophene-2-carbaldehyde oxime

生成物 1

HCID 218213104-Bromo-5-nitrothiophene-2-carbonitrile収率 86%

試薬・触媒・溶媒 1

HCID 21899848Ethylacetate heptane溶媒

実験手順

A 5-L, three neck, round bottom flask equipped with a temperature probe, mechanical stirrer, and a reflux condenser was charged with 4-Bromo-5-nitro-thiophene-2-carbaldehyde oxime (Example 25: step c; 441.0 g, 1.76 mol). Acetic anhydride (2.5 L) was added causing an endothermic reaction from 22° C. to 17° C. The resulting yellow slurry was heated to reflux. At 100° C. the reaction became a black solution. After 2 hours at 130° C., TLC analysis (2:1 heptane/EtOAc) showed reaction completion and the heat was removed. The mixture was transferred to a rotary evaporator and concentrated to dryness. The residue was diluted with CH2Cl2 (3L), and H2O (3L). The layers were separated and the organic layer was washed with H2O (3L), dried over MgSO4, and concentrated to give the desired title compound as a tan solid (350.85 g, 86%). 1H-NMR (DMSO): δ 8.3 (1H, s).

後処理

  1. customan endothermic reaction from 22° C. to 17° C
  2. temperatureThe resulting yellow slurry was heated to reflux
  3. customAt 100° C.
  4. customreaction completion
  5. customthe heat was removed
  6. customThe mixture was transferred to a rotary evaporator
  7. concentrationconcentrated to dryness
  8. additionThe residue was diluted with CH2Cl2 (3L), and H2O (3L)
  9. customThe layers were separated
  10. washthe organic layer was washed with H2O (3L)
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-17af5b82b0ec4253837fcc1170ca83cd
出典データセット
uspto-grants-2008_06
特許番号
US07385066B2

反応ノート

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