Pyrazole → 1-(4-bromophenyl)-1H-pyrazole

HRID 1487937

Reaction equation

HRID 1487937 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[NH:9]1[CH:13]=[CH:12][CH:11]=[N:10]1.CNCCNC.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I.CC#N>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 115221-Bromo-4-iodobenzene

Product 1

HCID 104435641-(4-bromophenyl)-1H-pyrazoleYield 94.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
82 °C

Procedure

Into a 100-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a mixture of 1-bromo-4-iodobenzene (2.82 g, 9.97 mmol), 1H-pyrazole (680 mg, 9.99 mmol), CuI (380 mg, 2.00 mmol), DMEDA (430 μL, 4.00 mmol, 0.40 equiv), Cs2CO3 (6.52 g, 20.00 mmol) an CH3CN (40 mL). The resulting mixture was stirred overnight at 82° C. After cooling to ambient temperature, the solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:12) as the eluent to yield the title compound as a white solid (2.1 g, 94%).

Workup

  1. customInto a 100-mL round-bottom flask, which was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureAfter cooling to ambient temperature
  4. customthe solids were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:12) as the eluent

Sources & evidence

ORD record
ord-79947f4bba6a4c42af0fa5cabd864385
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Linked notes

Loading…