3-fluoro-4-(1H-pyrazol-1-yl)aniline → 2-Bromo-5-fluoro-4-(pyrazol-1-yl)phenylamine

HRID 2184059노트

반응식

HRID 2184059 반응식
[F:1][C:2]1[CH:3]=[C:4]([NH2:13])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1.[Br-:14].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>O1CCCC1.CCOCC>[Br:14][C:5]1[CH:6]=[C:7]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[C:2]([F:1])=[CH:3][C:4]=1[NH2:13]

참가 물질

5

반응물 2

HCID 107259813-fluoro-4-(1H-pyrazol-1-yl)anilineHCID 21124087Pyridiniumtribromide

생성물 1

HCID 223295562-Bromo-5-fluoro-4-(pyrazol-1-yl)phenylamine

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 3-fluoro-4-(pyrazol-1-yl)phenylamine (2.56 g, 14.5 mmol) in tetrahydrofuran (50 ml) was added dropwise a solution of pyridinium tribromide (5.09 g, 15.9 mmol) in tetrahydrofuran (50 ml). The mixture was stirred for 1 h at room temperature then diluted with ether (250 ml). After stirring for a further 30 min the precipitate was filtered and washed with ether (50 ml×2). The white solid was dissolved in water (200 ml) and extracted with ethyl acetate (100 ml×3). The combined organic phases were dried over magnesium sulphate, filtered and the solvent removed to leave an orange oil. Purification by chromatography on silica gel eluting with dichloromethane gave 2-bromo-5-fluoro-4-(pyrazol-1-yl)phenylamine as a white solid: m/z (ES+) 256 and 258 (M++H).

후처리

  1. stirringAfter stirring for a further 30 min the precipitate
  2. filtrationwas filtered
  3. washwashed with ether (50 ml×2)
  4. dissolutionThe white solid was dissolved in water (200 ml)
  5. extractionextracted with ethyl acetate (100 ml×3)
  6. dry with materialThe combined organic phases were dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto leave an orange oil
  10. customPurification by chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-74acf7d9084446ae86e9cd7725be222f
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900215B2

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