1-(1,1-Difluoroethyl)-3-nitrobenzene → 3-(1,1-Difluoroethyl)aniline

HRID 1640139노트

반응식

HRID 1640139 반응식
[F:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1)([F:4])[CH3:3]>CC(O)=O.CCOC(C)=O.[Zn]>[F:1][C:2]([C:5]1[CH:6]=[C:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1)([F:4])[CH3:3]

참가 물질

5

반응물 1

HCID 108778561-(1,1-Difluoroethyl)-3-nitrobenzene

생성물 1

HCID 234450923-(1,1-Difluoroethyl)aniline

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(1,1-difluoroethyl)-3-nitrobenzene (2.75 g, 14.7 mmol) in AcOH (30 mL) was added zinc (10.0 g, 153 mmol). The reaction mixture was allowed to stir at rt overnight. The mixture was diluted with EtOAc (40 mL) and filtered through Celite. The filtrate was concentrated. The residue was diluted with DCM (20 mL), washed with saturated NaHCO3 (20 mL) and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(1,1-difluoroethyl)benzenamine as light brown oil. 1H NMR (300 MHz, DMSO) δ 7.21 (dd, 1H), 6.89 (s, 1H), 6.80 (d, 1H), 6.79 (d, 1H), 186 (t, 3H); LCMS: ES+ 158.1.

후처리

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated
  3. additionThe residue was diluted with DCM (20 mL)
  4. washwashed with saturated NaHCO3 (20 mL) and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-3c60a7b919394ee2ae5c20f9e6d43e43
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110687B2

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