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

HRID 1167464Notes

Reaction equation

HRID 1167464 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-de1496b6d1de429cb8e694e59e338108
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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