Pyrazole → 1-(3-Bromophenyl)-1H-pyrazole

HRID 881975노트

반응식

HRID 881975 반응식
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](F)[CH:10]=1>CN(C=O)C>[Br:8][C:9]1[CH:10]=[C:11]([N:3]2[CH:7]=[CH:6][CH:5]=[N:4]2)[CH:12]=[CH:13][CH:14]=1

참가 물질

5

반응물 3

HCID 1048PyrazoleHCID 140821-Bromo-3-fluorobenzeneHCID 24758Sodium hydride

생성물 1

HCID 71278041-(3-Bromophenyl)-1H-pyrazole수율 47.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a suspension of sodium hydride (3.52 g, 88 mmol) in DMF (40 ml), was added pyrazole (3.0 g, 44 mmol) in portions. After stirring at room temperature for 30 minutes, 1-bromo-3-fluorobenzene (9.3 g, 53 mmol) in DMF (20 ml) was added dropwise and the resulting mixture was stirred for 2 hours at 130° C. The mixture was cooled and quenched by the addition of a saturated aqueous NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified using normal phase chromatography, eluting with petroleum ether containing 10% ethyl acetate to give 1-(3-bromophenyl)-1H-pyrazole (4.7 g) as yellow solid.

후처리

  1. stirringthe resulting mixture was stirred for 2 hours at 130° C
  2. temperatureThe mixture was cooled
  3. customquenched by the addition of a saturated aqueous NH4Cl solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified
  9. washeluting with petroleum ether containing 10% ethyl acetate

출처 및 근거

ORD 기록
ord-104a73e2b85e4058b713d4205888236d
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993757B2

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