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Water → HCID 67501770, Verbindung

HRID 1625208
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1625208
[H-].[Na+].[F:3][C:4]([F:25])([F:24])[C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[C:14]2[CH:15]=[N:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:7][N:6]=1.[Br:26][C:27]1[CH:34]=[C:33](F)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30].O>CN(C)C=O>[Br:26][C:27]1[CH:34]=[C:33]([N:7]2[C:8]3=[N:9][CH:10]=[CH:11][C:12]([C:14]4[CH:15]=[N:16][C:17]5[C:22]([CH:23]=4)=[CH:21][CH:20]=[CH:19][CH:18]=5)=[C:13]3[C:5]([C:4]([F:24])([F:3])[F:25])=[N:6]2)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1189392-Bromo-4-fluorobenzonitrileHCID 178506293HCID 178506293, Verbindung

Produkt 1

HCID 67501770HCID 67501770, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

Sodium hydride (0.183 g, a 55% dispersion in paraffin liquid) was added to a solution of compound (1d) (0.940 g) in N,N-dimethylformamide (hereinafter referred to as DMF, 6 mL) at room temperature, followed by stirring for 30 min. Subsequently, 2-bromo-4-fluorobenzonitrile (0.838 g) was added to the reaction solution, followed by stirring at 60° C. for 1 hr. After cooling, water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated saline in this order and was dried over anhydrous sodium sulfate. After distillation of the solvent, the residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (1e) (0.56 g, 38%) as a white solid.

Aufarbeitung

  1. customat room temperature
  2. stirringby stirring at 60° C. for 1 hr
  3. temperatureAfter cooling
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water and saturated saline in this order
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationAfter distillation of the solvent
  8. customthe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-7d862ba486fe43bb8c0dda058497daf8
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08779142B2

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