4-Bromo-2,6-difluoroaniline → 5-Bromo-1,3-difluoro-2-nitrobenzene

HRID 217140

反応式

HRID 217140 の反応式
B1([O-])OO1.[OH2:5].[OH2:6].O.O.[Na+].[Br:10][C:11]1[CH:17]=[C:16]([F:18])[C:14]([NH2:15])=[C:13]([F:19])[CH:12]=1>C(O)(=O)C>[Br:10][C:11]1[CH:17]=[C:16]([F:18])[C:14]([N+:15]([O-:6])=[O:5])=[C:13]([F:19])[CH:12]=1

参加物

4

反応物 2

HCID 6101914-Bromo-2,6-difluoroanilineHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

生成物 1

HCID 213354875-Bromo-1,3-difluoro-2-nitrobenzene

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
55 °C

実験手順

To a suspension of sodium perborate tetrahydrate (1.04 g, 5 mmol) in acetic acid (20 mL), stirred at 55° C., was added a solution of 4-bromo-2,6-difluoroaniline in acetic acid (10 mL) over 1 hour in a dropwise fashion. After stirring at 55° C. for an additional 3 hours, the solution was allowed to cool to room temperature and filtered. The filtrate was poured into ice, and extracted twice with ethyl acetate. The combined organic extracts were washed successively with 5×100-mL portions of water, brine, dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel eluted with ethyl acetate:hexanes (1:20) to afford 780 mg of the titel compound as a tan solid. 1H NMR (CDCl3) δ 7.32 (dt, 2H).

後処理

  1. stirringAfter stirring at 55° C. for an additional 3 hours
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. additionThe filtrate was poured into ice
  5. extractionextracted twice with ethyl acetate
  6. washThe combined organic extracts were washed successively with 5×100-mL portions of water, brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by column chromatography over silica gel
  10. washeluted with ethyl acetate:hexanes (1:20)

出典と根拠

ORDレコード
ord-4a8ae26595264efab51e22f21f533939
出典データセット
uspto-grants-2012_06
特許番号
US08193352B2

関連ノート

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