Ammonium Chloride → HCID 86713632, Verbindung

HRID 1257189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257189
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl-].[NH4+]>CCO.[Fe]>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([Br:1])=[C:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 68984776HCID 68984776, Verbindung

Produkt 1

HCID 86713632HCID 86713632, VerbindungAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A solution of ethyl 2-(2-bromo-4-fluoro-5-nitrophenyl)acetate (2.127 g, 6.95 mmol) in EtOH (70 mL) was treated with iron powder (3.88 g, 69.5 mmol) and satd ammonium chloride (14.48 mL, 69.5 mmol) and heated to 55° C. for 1 h. The mixture was cooled to RT, filtered through a pad of diatomaceous earth, rinsed well with EtOH and the organics concentrated under reduced pressure. The resulting aqueous residue was treated with satd. NaHCO3, extracted with EtOAc (2×) and the combined organics were washed with water, dried (MgSO4), and concentrated to afford ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate (1.792 g, 93% yield) as an amber oil. 1H NMR (400 MHz, DMSO-d6): δ 7.25 (d, 1H), 6.76 (d, 1H), 5.35 (s, 2H), 4.08 (q, 2H), 3.61 (s, 2H), 1.18 (t, 3H); MS (ESI) m/z: 278.0 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered through a pad of diatomaceous earth
  3. washrinsed well with EtOH
  4. concentrationthe organics concentrated under reduced pressure
  5. additionThe resulting aqueous residue was treated with satd
  6. extractionNaHCO3, extracted with EtOAc (2×)
  7. washthe combined organics were washed with water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-01a5b211aa34456a8e6a1ab45797353d
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461179B1

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