Pyridine → 1-Fluoro-2-isocyanato-4-methoxy-5-methyl-benzene

HRID 1691815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691815
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH2:11].N1C=CC=CC=1.[C:18](Cl)(Cl)=[O:19]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[N:11]=[C:18]=[O:19]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 6371PhosgeneHCID 593777852-Fluoro-5-methoxy-4-methylaniline

Produkt 1

HCID 593778971-Fluoro-2-isocyanato-4-methoxy-5-methyl-benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-Fluoro-5-methoxy-4-methyl-phenylamine (78 mg, 0.50 mmol) was dissolved in 10 ml of toluene at room temperature. DMAP (1 eq, 61 mg), pyridine (1.3 eq, 0.06 ml) were added followed by phosgene (1.33 eq, 0.34 ml, 20% solution in toluene). The mixture was allowed to stir at room temperature for 3 hours, forming a fine white precipitate. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was diluted with dichloromethane and concentrated in vacuo again to give 1-fluoro-2-isocyanato-4-methoxy-5-methyl-benzene (90 mg, quantitative) as a clear oil.

Aufarbeitung

  1. customforming a fine white precipitate
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with dichloromethane
  5. concentrationconcentrated in vacuo again

Quellen und Nachweise

ORD-Eintrag
ord-342da76530f74e97a896651691cf49f5
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153809B2

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