Sodium hydride → 3-Fluoro-4-(3-cyano-1-pyrrolyl)nitrobenzene

HRID 1167464ノート

反応式

HRID 1167464 の反応式
[C:1]([C:3]1[CH:7]=[CH:6][NH:5][CH:4]=1)#[N:2].[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1F.[H-].[Na+]>CN(C=O)C>[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1[N:5]1[CH:6]=[CH:7][C:3]([C:1]#[N:2])=[CH:4]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 5642063-Cyanopyrrole

生成物 1

HCID 229960033-Fluoro-4-(3-cyano-1-pyrrolyl)nitrobenzene収率 41.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-Cyanopyrrole (3.6 g, 39.1 mmol , CE Loader et al, Can. J. Chem., 1981, 59, 2673) and 3,4-difluoronitrobenzene (6.5 g, 40.9 mmol) were dissolved in DMF (50 ml) and cooled in an ice-bath. The mixture was stirred and sodium hydride (60% in oil, 1.6 g, 40 mmol) added over 20 minutes. After allowing the mixture to come to ambient temperature, it was heated to 650 for 1 hour. Solvent was evaporated, the residue triturated with water, and filtered. The crude solide was purified by flash chromatography on silica, eluting with dichloromethane. Relevant fractions were combined to give the title product (3.75 g), mp 117-119°.

後処理

  1. temperaturecooled in an ice-bath
  2. customto come to ambient temperature
  3. temperatureit was heated to 650 for 1 hour
  4. customSolvent was evaporated
  5. customthe residue triturated with water
  6. filtrationfiltered
  7. customThe crude solide was purified by flash chromatography on silica
  8. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-de1496b6d1de429cb8e694e59e338108
出典データセット
uspto-grants-2003_09
特許番号
US06617339B1

反応ノート

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