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

HRID 1769203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1769203
[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.N1(C2CCCCCCCC2)CCCCCCCC1>[Br:15][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]#[N:14])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

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

Produkt 1

HCID 200928574-(3-Cyano-2-thienyl)benzyl bromideAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 18706763HCID 18706763, VerbindungKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-methylphenyl)-3-cyanothiophene (1.5 g, 7.5 mmol), N-bromosuccinimide (1.34 g, 7.5 mmol), and azabicyclononane (20 mg) in carbon tetrachloride was irradiated with UV light for one hour. The reaction mixture was cooled, and the solid filtered off. The filtrate was concentrated, and the residue purified by flash chromatography, eluting with 5% ethyl acetate/hexane, to yield 2-(4-bromomethylphenyl)-3-cyanothiophene 1.4 g, m.p. 68-75 (slightly impure, used as such).

Aufarbeitung

  1. customwas irradiated with UV light for one hour
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe solid filtered off
  4. concentrationThe filtrate was concentrated
  5. customthe residue purified by flash chromatography
  6. washeluting with 5% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-70b25ef575a847cf88367ef29622c2c9
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380739

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