Pyridine → 1-Bromo-2-isocyanato-4,5-dimethoxybenzene

HRID 1691801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691801
[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:3]=1[NH2:4].N1C=CC=CC=1.[C:19](Cl)(Cl)=[O:20]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:3]=1[N:4]=[C:19]=[O:20]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 6371PhosgeneHCID 4140762-Bromo-4,5-dimethoxyaniline

Produkt 1

HCID 582002611-Bromo-2-isocyanato-4,5-dimethoxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-Bromo-4,5-dimethoxyaniline (464 mg, 2.0 mmol) was dissolved in 10 ml of toluene at room temperature. DMAP (1 eq, 245 mg), pyridine (1.3 eq, 0.22 ml) were added followed by phosgene (1.33 eq, 1.33 ml of a 20% solution in toluene). The mixture was heated to 90° C. for 4 hours. Upon cooling, the mixture was filtered and the filtrate was concentrated in vacuo to give 1-bromo-2-isocyanato-4,5-dimethoxy-benzene (542 mg, quantitative) as a light brown oil.

Aufarbeitung

  1. temperatureUpon cooling
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-31028c7dcc3b4cf482d1bb2a2f2e884b
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153809B2

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