N-bromobutanimide → 4-(3-Cyano-2-thienyl)benzyl bromide

HRID 1708419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1708419
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:13]([C:12]1[CH:11]=[CH:10][S:9][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([CH2:1][Br:15])=[CH:7][CH:6]=1)#[N:14]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 200928362-(4-Methylphenyl)thiophene-3-carbonitrile

Produkt 1

HCID 200928574-(3-Cyano-2-thienyl)benzyl bromideAusbeute 40,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

24.5 g of 2-(4-methylphenyl)-3-cyanothiophene, prepared in E), are dissolved in 200 ml of carbon tetrachloride. 21.9 g of N-bromosuccinimide are added, as well as 0.1 g of benzoyl peroxide. The mixture is heated to reflux for 24 hours. The crystals of succinimide are filtered off and the solvent is evaporated off under vacuum. The residue is taken up in a mixture of hexane and ethyl acetate and the solution is kept in a freezer for 24 hours. The crystals formed are drained to give 14 g of 4-(3-cyano-2-thienyl)benzyl bromide in the form of crystals of melting point 80° C.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 24 hours
  3. filtrationThe crystals of succinimide are filtered off
  4. customthe solvent is evaporated off under vacuum
  5. additionThe residue is taken up in a mixture of hexane and ethyl acetate
  6. customThe crystals formed

Quellen und Nachweise

ORD-Eintrag
ord-ed3c5c127f314628911976e96671415d
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05358950

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