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

HRID 217140

반응식

HRID 217140 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

반응 조건

온도
55 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4a8ae26595264efab51e22f21f533939
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193352B2

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