Methane → HCID 64429773, compound

HRID 1987704Notes

Reaction equation

HRID 1987704 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[I:11][C:12]1[CH:13]=[N:14][NH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C>N1C=CC=CC=1.ClCCl.[Cu]=O>[I:11][C:12]1[CH:13]=[N:14][N:15]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:16]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 770224-Iodopyrazole

Product 1

HCID 64429773HCID 64429773, compoundYield 76.2%

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-fluoro-2-nitrobenzene (14.5 g, 0.1 mol), 4-iodopyrazole (20 g, 0.1 mol), potassium carbonate anhydrous (14 g, 0.1 mol) and catalytical amounts of copper(II) oxide in pyridine (35 ml) was heated to reflux for 16 hours. After cooling, the mixture was diluted with dichloromethane (1 litre). Activated charcoal (12 g) was then added and the mixture was heated to reflux for 1 hour. After cooling, it was filtered through celite. The filtrate was evaporated and the remaining oil was purified by silica gel chromatography using ethyl acetate and hexane as eluents, giving 4-iodo-1-(2-nitro-phenyl)-1H-pyrazole (24 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. temperatureAfter cooling
  4. temperaturethe mixture was heated
  5. temperatureto reflux for 1 hour
  6. temperatureAfter cooling
  7. filtrationit was filtered through celite
  8. customThe filtrate was evaporated
  9. customthe remaining oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7d6a4bdadb0b4c59a90caaacc71c1312
Source dataset
uspto-grants-2009_06
Patent number
US07553798B2

Reaction notes

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