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

HRID 586334ノート

反応式

HRID 586334 の反応式
[F:1][C:2]1[C:3]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[CH:4][CH:5]=[C:6]([NH2:8])[CH:7]=1.[Br-:14].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>O1CCCC1.C(OCC)C>[Br:14][C:5]1[CH:4]=[C:3]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)[C:2]([F:1])=[CH:7][C:6]=1[NH2:8]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 5-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 diethyl ether (250 ml). After stirring for a further 30 min the precipitate was filtered and washed with diethyl 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 (silica gel, CH2Cl2) gave 2-bromo-5-fluoro-4(pyrazol-1-yl)phenylamine as a white solid: MS (ES+) m/z 256 and 258 [M+H]+.

後処理

  1. stirringAfter stirring for a further 30 min the precipitate
  2. filtrationwas filtered
  3. washwashed with diethyl 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 (silica gel, CH2Cl2)

出典と根拠

ORDレコード
ord-c4aad5e859c34d37ae49607307fb9a2a
出典データセット
uspto-grants-2005_08
特許番号
US06936608B2

反応ノート

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