Water → 2-Nitro-benzo[B]thiophene-3-carbonitrile

HRID 131371

Reaktionsgleichung

Reaktionsgleichung von HRID 131371
Br[C:2]1[C:3]2[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[N+:7]([O-:9])=[O:8].[Cu](C#N)[C:15]#[N:16].O>CN(C=O)C>[N+:7]([C:6]1[S:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=2[C:2]=1[C:15]#[N:16])([O-:9])=[O:8]

Komponenten

5

Edukt 3

HCID 962WaterHCID 2970503-Bromo-2-nitro-benzo(b)thiopheneHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 210935092-Nitro-benzo[B]thiophene-3-carbonitrileAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Combine 3-bromo-2-nitro-benzo[b]thiophene (33.0 g, 127.4 mmol), copper cyanide (17.1 g, 191.1 mmol) in DMF (150 mL), heat to 120° C. for three hours. The reaction cool to RT, pour on ice, then filter. The filter cake wash with dichloromethane. The organic layer separate and dry over MgSO4, evaporation to give a DMF solution. Add water (400 mL) and the yellow solid precipitate out. After filtration, obtain a brownish solid (23.5 g, 90%). Mass spectrum (m/e): 205 (M+1); 1HNMR (300 MHz, DMSO-d6) δ: 7.78(m, 2H), 8.04(d, 1H), 8.29(d, 1H). 3CNMR(75 MHz, DMSO-d6) δ ppm: 105.9, 112.1, 125.0, 125.2, 128.8, 131.2, 135.9, 137.8, 158.0.

Aufarbeitung

  1. additionpour on ice
  2. filtrationfilter
  3. washThe filter cake wash with dichloromethane
  4. customThe organic layer separate
  5. dry with materialdry over MgSO4, evaporation
  6. customto give a DMF solution
  7. filtrationAfter filtration

Quellen und Nachweise

ORD-Eintrag
ord-30f11efcfd59462f8234f9b423080c2f
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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