Ammonia → ({3-[(3-Bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine

HRID 1875147

Reaktionsgleichung

Reaktionsgleichung von HRID 1875147
[NH3:1].[Br:2][C:3]1[CH:4]=[C:5]([O:10][C:11]2[C:16]([F:17])=[C:15]([CH2:18]Br)[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:6]=[C:7]([Cl:9])[CH:8]=1>C(Cl)Cl>[Br:2][C:3]1[CH:4]=[C:5]([O:10][C:11]2[C:16]([F:17])=[C:15]([CH2:18][NH2:1])[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:6]=[C:7]([Cl:9])[CH:8]=1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 684836772-[(3-Bromo-5-chlorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene

Produkt 1

HCID 68487182({3-[(3-Bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amineAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a flask containing ammonia (7.0 M solution in methanol) (132 ml, 927 mmol) was added a solution of 2-[(3-bromo-5-chlorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene (4.97 g, 11.59 mmol) in DCM (15 ml) dropwise and the mixture was stirred overnight at room temperature. The solvent was removed and the crude material was purified via silica gel chromatography to give ({3-[(3-bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine (3.70 g, 10.14 mmol, 87% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.34-7.85 (m, 3H), 7.06 (s, 1H), 6.99 (t, 1H), 3.72 (s, 2H), 1.85 (s, 2H).

Aufarbeitung

  1. customThe solvent was removed
  2. customthe crude material was purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e58c92c1af8b416c9443c4cfa6664a86
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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