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

HRID 1640139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640139
[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]

Komponenten

5

Edukt 1

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

Produkt 1

HCID 234450923-(1,1-Difluoroethyl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3c60a7b919394ee2ae5c20f9e6d43e43
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110687B2

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