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

HRID 1167464노트

반응식

HRID 1167464 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-de1496b6d1de429cb8e694e59e338108
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617339B1

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