4-Cyclopropyl-1-fluoro-2-nitrobenzene → 5-Cyclopropyl-2-fluoroaniline

HRID 1898323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898323
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([F:10])=[C:6]([N+:11]([O-])=O)[CH:5]=2)[CH2:3][CH2:2]1>C(O)(=O)C.[Fe]>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH:5]=2)[NH2:11])[CH2:3][CH2:2]1

Komponenten

4

Edukt 1

HCID 569685734-Cyclopropyl-1-fluoro-2-nitrobenzene

Produkt 1

HCID 675036775-Cyclopropyl-2-fluoroanilineAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 4-cyclopropyl-1-fluoro-2-nitrobenzene (0.700 g, 4.26 mmol) in acetic acid (6.0 mL) was added iron powder (1.0 g). The reaction mass was stirred at RT for 2 h. The reaction mass was quenched in water and basified with NaHCO3, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.500 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 0.50-0.52 (m, 2H), 0.83-0.85 (m, 2H), 1.71-1.74 (m, 1H), 4.97 (s, 2H), 6.21 (m, 1H), 6.44 (d, J=9.0 Hz, 1H), 6.77-6.84 (m, 1H).

Aufarbeitung

  1. customThe reaction mass was quenched in water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b0d24f65b9944f6b8e8fe20afcc73240
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08519149B2

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