1-Fluoro-3-nitrobenzene → HCID 59599657, compound

HRID 2266412Notes

Reaction equation

HRID 2266412 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[H-].[Na+].[N+:9]([C:12]1[CH:13]=[C:14](F)[CH:15]=[CH:16][CH:17]=1)([O-:11])=[O:10]>CN(C=O)C>[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:9]([O-:11])=[O:10])[CH:17]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 98231-Fluoro-3-nitrobenzeneHCID 24758Sodium hydrideHCID 178418934HCID 178418934, compound

Product 1

HCID 59599657HCID 59599657, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 4-bromo-imidazole (32 g; 217.7 mmol) in DMF (300 mL) was carefully added NaH (60% dispension; 10.8 g; 270 mmol) such that the temperature did not exceed 30° C. The slurry was stirred for 20 min after which 3-nitro-fluorobenzene 35 mL; 329 mmol) was added. The reaction mixture was stirred for another 30 min, heated to 150° C. and left with stirring overnight. The reaction mixture was poured onto 750 mL of ice-water under stirring. The precipitate was isolated by filtration, washed with H2O, air-dried and trituated with a diethyl ether-petrol ether (bp=80-100° C.) mixture (100 mL+100 mL) to give after filtration and drying of the solid 70 g crude product.

Workup

  1. customdid not exceed 30° C
  2. addition329 mmol) was added
  3. waitleft
  4. stirringwith stirring overnight
  5. stirringunder stirring
  6. customThe precipitate was isolated by filtration
  7. washwashed with H2O
  8. customair-dried
  9. customto give
  10. filtrationafter filtration
  11. dry with materialdrying of the solid 70 g crude product

Sources & evidence

ORD record
ord-d64475906b9944ee989973995404a01d
Source dataset
uspto-grants-2010_12
Patent number
US07858649B2

Reaction notes

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