4-Isopropylnitrobenzene → 2-Bromo-4-nitro-1-(propan-2-yl)benzene

HRID 59581

Reaktionsgleichung

Reaktionsgleichung von HRID 59581
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:13]Br.S([O-])(O)=O.[Na+]>[Fe](Cl)(Cl)Cl.O>[Br:13][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[CH:10]([CH3:12])[CH3:11]

Komponenten

6

Edukt 3

HCID 157494-IsopropylnitrobenzeneHCID 24408BromineHCID 23665763Sodium Bisulfite

Produkt 1

HCID 215316212-Bromo-4-nitro-1-(propan-2-yl)benzeneAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24380Iron chloride (FeCl3)KatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of p-nitrocumene (X) (50 g, 0.300 mol, GC purity: 99.1%) and iron(III) chloride was heated to 40° C. and bromine (59.92 g, 0.375 mol) was added dropwise over a period of 3 hours. The reaction mixture was poured into 120 ml of water, sodium hydrogensulphite (40% strength in water, 20.81 g, 0.078 mol) was added dropwise and the mixture was extracted with 100 ml of chlorobenzene. After phase separation, the chlorobenzene phase was washed with 100 ml of 5% strength aqueous HCl. Removal of the chlorobenzene under reduced pressure gave 2-bromo-1-isopropyl-4-nitrobenzene (74.05 g, 96.9 GC-% by area, 98% of theory) as a yellow oil.

Aufarbeitung

  1. additionwas added dropwise
  2. extractionthe mixture was extracted with 100 ml of chlorobenzene
  3. customAfter phase separation
  4. washthe chlorobenzene phase was washed with 100 ml of 5% strength aqueous HCl
  5. customRemoval of the chlorobenzene under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0f8ae6945fcf438e85cf6fc99893b49b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440908B2

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