HCID 21584088, Verbindung → HCID 21584080, Verbindung

HRID 583031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583031
[C:1]1([S:7][C:8]2([O:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=3[N+:23]([O-])=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O.C(O)(=O)C.[Fe]>[C:1]1([S:7][C:8]2([O:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:20])([F:21])[F:22])=[CH:14][C:13]=3[NH2:23])[CH2:9][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 1

HCID 21584088HCID 21584088, Verbindung

Produkt 1

HCID 21584080HCID 21584080, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Iron powder (13.5 g, 241 mmol) was added to a suspension of 2-(1-phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)nitrobenzene (Description 4, 11.27 g, 30.1 mmol) in water (300 mL) and acetic acid (75 mL) and the mixture was stirred at 80° C. overnight. The mixture was cooled and filtered through celite, washing with ether. The filtrate was extracted with ether, the combined organic fractions were washed with aqueous sodium hydroxide (1M), dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/Et2O (90:10 increasing to 80:20), to give the title compound as a yellow solid (8 g, 78%). 1H NMR (360 MHz, CDCl3) δ7.48 (2 H, m), 7.34-7.23 (3 H, m), 7.15 (1 H, d, J 8.74 Hz), 6.60-6.56 (2 H, m), 3.78 (2 H, br s), 1.49-1.46 (2 H, m), and 1.39-1.35 (2 H, m).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. washwashing with ether
  4. extractionThe filtrate was extracted with ether
  5. washthe combined organic fractions were washed with aqueous sodium hydroxide (1M)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with hexane/Et2O (90:10 increasing to 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-c5e4c3751384441ca00a4d06307ab623
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929054

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