Bromine → 2-Bromo-6-nitro-4-phenoxy-phenylamine

HRID 1466473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1466473
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[NH2:17])([O-:3])=[O:2].[Br:18]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Br:18][C:6]1[CH:7]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[NH2:17]

Komponenten

5

Edukt 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 51737522-Nitro-4-phenoxyaniline

Produkt 1

HCID 684774322-Bromo-6-nitro-4-phenoxy-phenylamineAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Nitro-4-phenoxy-phenylamine (2.3 g, 10 mmol) prepared in Preparation 1 was dissolved in DCM (30 mL), Br2 (720 ul, 35%) was added thereto at 0° C., and the mixture was stirred for 2 h. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added. The resulting mixture was extracted with EtOAc, and dried over MgSO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (2.84 g, Yield 92%).

Aufarbeitung

  1. additionwas added
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-13d261a1ecb548ee8459bb02cd9ef85c
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000028B2

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