2-Fluoro-5-nitrobenzonitrile → 5-Amino-2-fluorobenzonitrile

HRID 376429

Reaktionsgleichung

Reaktionsgleichung von HRID 376429
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:3]=1[C:4]#[N:5]>C(OCC)(=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

3

Edukt 1

HCID 5194172-Fluoro-5-nitrobenzonitrile

Produkt 1

HCID 27376735-Amino-2-fluorobenzonitrileAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-fluoro-5-nitrobenzonitrile (2.0 g, 12 mmol) in ethyl acetate(50 mL) was added stannous chloride (27.0 g, 120 mmol). The reaction mixture was stirred at reflux 1.5 h, then cooled to room temperature. Partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate(150 mL). Organic phase was separated and washed with water (5×75 mL), brine (75 mL); dried over sodium sulfate (anhy.); filtered and concentrated to give 2-fluoro-5-aminobenzonitrile (1.4 g) as pure compound.

Aufarbeitung

  1. temperatureat reflux 1.5 h
  2. customPartitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate(150 mL)
  3. customOrganic phase was separated
  4. washwashed with water (5×75 mL), brine (75 mL)
  5. dry with materialdried over sodium sulfate (anhy.)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8478ae9ce00f4aafb8ce937a724cad71
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020357

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