Dimethylformamide → 3-[(Tert-butoxy)carbonyl]-5-nitrobenzoic acid

HRID 562524

Reaktionsgleichung

Reaktionsgleichung von HRID 562524
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([O-:3])=[O:2].CN(C)C=O>C1(C)C=CC=CC=1>[C:6]([O:14][C:13](=[O:15])[C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[CH:7]=1)([CH3:13])([CH3:7])[CH3:5]

Komponenten

4

Edukt 2

HCID 6228DimethylformamideHCID 120695-Nitroisophthalic acid

Produkt 1

HCID 693810873-[(Tert-butoxy)carbonyl]-5-nitrobenzoic acidAusbeute 248,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension of 5-nitro-isophthalic acid (5.0 g, 23.7 mmol) in dry toluene (100 ml) at 110° C. was added dimethylformamide di-t-butylacetale (3.4 ml, 71 mmol) drop wise over 60 min. Heating was continued for 45 min and the reaction mixture was left at Rt over night. The precipitated starting material was removed by filtration. The filtrate was concentrated to give a yellow oil (7.88 g). This was purified by flash chromatography using EtOAc/Hept 1:2 and EtOAc/Hept 1:2+5% AcOH in two portions to give the title compound in 38% yield (2.38 g)

Aufarbeitung

  1. temperatureHeating
  2. waitthe reaction mixture was left at Rt over night
  3. customwas removed by filtration
  4. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-43d77f5ddfbd4af4bf35a78f513804a3
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067362B2

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