Ammonium Chloride → 3-Chloro-4-(3-fluorobenzyloxy)aniline

HRID 38507

Reaktionsgleichung

Reaktionsgleichung von HRID 38507
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1.[Cl-].[NH4+]>C(O)C.O.[Zn]>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[NH2:8]

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 70592692-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzene

Produkt 1

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineAusbeute 120,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-chloro-1-[(3-fluorobenzyl)oxy]-4-nitrobenzene from Example 3A (8.70 g, 25.1 mmol) in ethanol (150 mL) was added zinc powder (10.1 g, 154 mmol), and the mixture was heated to 60° C. A solution of ammonium chloride (3.30 g, 61.8 mmol) in water (30 mL) was added dropwise, and the reaction was stirred for additional 2 h at this temperature. The mixture was filtered through Celite®, and the solvent was removed in vacuo. The residue was triturated with water, and the precipitate was collected by suction filtration, washed with water and dried to yield 7.63 g (98%) of the aniline.

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite®
  2. customthe solvent was removed in vacuo
  3. customThe residue was triturated with water
  4. filtrationthe precipitate was collected by suction filtration
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dd81d357f3de43e5a595a46905d3e911
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524722B2

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