Ammonium Chloride → Tert-butyl 4-amino-2-fluorobenzoate

HRID 891458

Reaktionsgleichung

Reaktionsgleichung von HRID 891458
[F:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:7]([O:6][C:4](=[O:5])[C:3]1[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][C:2]=1[F:1])([CH3:10])([CH3:8])[CH3:9]

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 10243388Tert-butyl 2-fluoro-4-nitrobenzoate

Produkt 1

HCID 10058989Tert-butyl 4-amino-2-fluorobenzoateAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Tert-butyl 2-fluoro-4-nitrobenzoate (24.2 g, 0.100 mol) was added to a warm (95° C.) solution of ammonium chloride (53.5 g, 1.00 mol), dissolved in ethanol (300 ml) and water (150 ml). Iron powder (325 mesh, 16.8 g, 0.300 mol) was added with stirring in small portions over ca. 1 h. The reaction mixture was stirred and heated at 95° C. for another 30 minutes and then filtered while still warm. The filter cake was washed thoroughly with excess ethanol. The filtrate and washings were diluted with water (1 L) and extracted with ether (3×150 ml). Combined ether extracts were washed with water and brine, dried (MgSO4), and evaporated to give the product as an off-white solid (21.1 g, 98%); mp 100-101° C. 1H NMR.

Aufarbeitung

  1. stirringThe reaction mixture was stirred
  2. filtrationfiltered
  3. temperaturewhile still warm
  4. washThe filter cake was washed thoroughly with excess ethanol
  5. additionThe filtrate and washings were diluted with water (1 L)
  6. extractionextracted with ether (3×150 ml)
  7. washCombined ether extracts were washed with water and brine
  8. dry with materialdried (MgSO4)
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-862ffcf498d247d3b3f67199f7422b21
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07002020B1

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