Hydrochloric Acid → 4-(4-Iodophenyl)benzonitrile

HRID 2372978

Reaktionsgleichung

Reaktionsgleichung von HRID 2372978
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Hg](C#N)[C:16]#[N:17].N1C=CC=CC=1.Cl>CN(C)C=O>[I:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:16]#[N:17])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 11591Mercuric cyanideHCID 763484,4'-Diiodo-1,1'-biphenyl

Produkt 1

HCID 13930054-(4-Iodophenyl)benzonitrileAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 15 g (33.2.10-3 mol) of 4,4'-diiodo-1,1'-biphenyl, 3.13 g (34.9.10-3 mol) of mercuric cyanide and 2.75 g (34.9.10-3 mol) of pyridine is heated at 200° C. for 15 minutes and 6 ml of dimethylformamide are then added to the mixture. After cooling, the reaction medium is hydrolyzed with a 1N aqueous solution of hydrochloric acid. The expected product is extracted with ethyl acetate. The organic phase obtained is washed with water until the pH of the washings is neutral, dried over magnesium sulfate and evaporated under vacuum. 3.28 g (yield: 33%) of a yellow solid are obtained after purification by flash chromatography using a chloroform/toluene mixture (1/1 v/v) as the eluent.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe expected product is extracted with ethyl acetate
  3. customThe organic phase obtained
  4. washis washed with water until the pH of the washings
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-416499616194444f888a6cad8972cf0f
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05101048

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