N-bromobutanimide → 5-(Bromomethyl)thiophene-2-carbonitrile

HRID 983384

Reaktionsgleichung

Reaktionsgleichung von HRID 983384
[CH3:1][C:2]1[S:6][C:5]([C:7]#[N:8])=[CH:4][CH:3]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][CH2:1][C:2]1[S:6][C:5]([C:7]#[N:8])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 3127335-Methylthiophene-2-carbonitrile

Produkt 1

HCID 105600165-(Bromomethyl)thiophene-2-carbonitrileAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 5-methylthiophene-2-carbonitrile (9.9 g, 80.5 mmol), benzoylperoxide (0.23 g, 0.95 mmol), and N-bromosuccinimide (15 g, 84.3 mmol) in carbontetrachloride (200 mL) was heated at reflux for 6 h. The resulting suspension was filtered and the filtrate diluted with dichloromethane (400 mL), washed with a saturated sodium bicarbonate solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (EtOAc: n-hexane, 1:4) to give the title compound as a yellow oil (14.0 g, 86%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. filtrationThe resulting suspension was filtered
  4. additionthe filtrate diluted with dichloromethane (400 mL)
  5. washwashed with a saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (EtOAc: n-hexane, 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-375028d805c444a8ab2f8e601bbaa48e
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06864249B2

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