Sodium Sulfide → 3-Bromo-4-isopropylaniline

HRID 59582

Reaktionsgleichung

Reaktionsgleichung von HRID 59582
[S-2].[Na+].[Na+].[S].[Br:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16]>C(O)(C)C>[Br:5][C:6]1[CH:11]=[C:10]([CH:9]=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16])[NH2:12]

Komponenten

5

Edukt 3

HCID 14804Sodium SulfideHCID 5362487SulfurHCID 215316212-Bromo-4-nitro-1-(propan-2-yl)benzene

Produkt 1

HCID 2807993-Bromo-4-isopropylanilineAusbeute 103,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A solution of sodium sulphide (31.2 g, 0.24 mol) and sulphur (7.7 g, 0.24 mol) was stirred at 80° C. for 15 minutes. Isopropanol (160 g) was subsequently added and the mixture was stirred at 75° C. for a further 15 minutes and 2-bromo-1-isopropyl-4-nitrobenzene (XI) (50 g, 0.19 mol) was finally added dropwise over a period of 30 minutes. After stirring for another 5 hours, the reaction was complete. For the work-up, the isopropanol was firstly distilled off and the remaining mixture was extracted with toluene/chlorobenzene. The combined organic phases were distilled under reduced pressure. 3-Bromo-4-isopropylaniline (42 g, 91 GC-% by area, 93% of theory) was obtained as a red oil.

Aufarbeitung

  1. stirringAfter stirring for another 5 hours
  2. distillationFor the work-up, the isopropanol was firstly distilled off
  3. extractionthe remaining mixture was extracted with toluene/chlorobenzene
  4. distillationThe combined organic phases were distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0b8cff70b7e74cb5865e34e425b77082
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440908B2

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