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

HRID 1487937노트

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HRID 1487937 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6342Acetonitrile용매

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온도
82 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-79947f4bba6a4c42af0fa5cabd864385
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428502B2

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