Tetrahydrofuran → 2-Nitro-4-(pentafluoroethyl)benzaldehyde

HRID 1873496노트

반응식

HRID 1873496 반응식
CN(C)/C=[CH:4]/[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19].C1C[O:25]CC1>P([O-])([O-])([O-])=O>[N+:18]([C:6]1[CH:7]=[C:8]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:10][C:5]=1[CH:4]=[O:25])([O-:20])=[O:19]

참가 물질

4

반응물 2

HCID 8028TetrahydrofuranHCID 86623311HCID 86623311, 화합물

생성물 1

HCID 573559322-Nitro-4-(pentafluoroethyl)benzaldehyde수율 52%

시약·촉매·용매 1

HCID 1061Phosphate용매

실험 절차

To a solution of crude (E)-N,N-dimethyl-2-(2-nitro-4-(perfluoroethyl)phenyl)ethenamine (12.2 g, 39.2 mmol) in THF (300 mL) and pH 7.2 phosphate buffer (300 mL) was added NaIO4 (29.3 g, 137.2 mmol). After 2.5 hours an aliquot (˜0.3 mL) was removed, filtered and dried. The proton NMR of this sample indicated that the reaction was complete. The solids were removed and the filter cake was washed with EtOAc. The filtrate was washed with brine (2×100 mL), dried and concentrated. The concentrate was purified via flash chromatography (100% hexane to 5% EtOAc) to provide 2-nitro-4-(perfluoroethyl)benzaldehyde (5.4 g, 52%).

후처리

  1. customAfter 2.5 hours an aliquot (˜0.3 mL) was removed
  2. filtrationfiltered
  3. customdried
  4. customThe solids were removed
  5. washthe filter cake was washed with EtOAc
  6. washThe filtrate was washed with brine (2×100 mL)
  7. customdried
  8. concentrationconcentrated
  9. customThe concentrate was purified via flash chromatography (100% hexane to 5% EtOAc)

출처 및 근거

ORD 기록
ord-731b193bc88b4a35adf0a108b3fa9867
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304407B2

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