Cyanogen Bromide → 4,5-Dichloro-2-(3,4-dichlorophenyl)pyrrole-1,3-dicarbonitrile

HRID 1033576

Reaktionsgleichung

Reaktionsgleichung von HRID 1033576
CC(C)([O-])C.[K+].[C:7]([C:9]1[C:13]([Cl:14])=[C:12]([Cl:15])[NH:11][C:10]=1[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)#[N:8].[N:24]#[C:25]Br>C1COCC1>[Cl:14][C:13]1[C:9]([C:7]#[N:8])=[C:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[N:11]([C:25]#[N:24])[C:12]=1[Cl:15]

Komponenten

5

Edukt 3

HCID 10476Cyanogen BromideHCID 1835554,5-dichloro-2-(3,4-dichlorophenyl)-1H-pyrrole-3-carbonitrileHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 150101564,5-Dichloro-2-(3,4-dichlorophenyl)pyrrole-1,3-dicarbonitrileAusbeute 64,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Potassium t-butoxide (617 mg, 55 mmol) is added in portions to a solution of 3-cyano-4,5-dichloro 2-(3,4-dichlorophenyl)pyrrole (1.52 g, 5 mmol) in anhydrous THF (20 mL). After 30 minutes, a solution of cyanogen bromide (583 mg, 5.5 mmol) in THF (1 mL) is added. The reaction mixture is stored at room temperature overnight. The solvent is removed in a rotary evaporator. The residue is treated with water and extracted with ethyl acetate. The organic layer is washed with water and saturated sodium chloride and dried (MgSO4). Evaporation and crystallization of the residue from ethyl acetate gives while crystals (1.07 g); mp 250.5°-252.0° C.; IR (nujol) 2255, 2245 cm-1 (CN); 13C NMR (DMSO-d6) 102.7 (N--CN), 113.7 (3-CN); Mass spectrum 331.9 (M+1).

Aufarbeitung

  1. waitThe reaction mixture is stored at room temperature overnight
  2. customThe solvent is removed in a rotary evaporator
  3. additionThe residue is treated with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with water and saturated sodium chloride
  6. dry with materialdried (MgSO4)
  7. customEvaporation and crystallization of the residue from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2a4f6d430cfc4aaf9f0e0611a7698463
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310938

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