Carbon tetrabromide → 5-(Bromomethyl)thiophene-2-carbonitrile

HRID 1597

Reaktionsgleichung

Reaktionsgleichung von HRID 1597
[C:1]([C:3]1[S:4][C:5]([CH2:8]O)=[CH:6][CH:7]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>C1COCC1>[C:1]([C:3]1[S:4][C:5]([CH2:8][Br:30])=[CH:6][CH:7]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 106068135-(Hydroxymethyl)thiophene-2-carbonitrile

Produkt 1

HCID 105600165-(Bromomethyl)thiophene-2-carbonitrileAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-cyano-5-(hydroxymethyl)thiophene (6.0 g, 43 mmol) in THF (50 mL) was added triphenylphosphine (15.7 g, 47 mmol) and carbon tetrabromide (12.3 g, 47 mmol). After stirring overnight under nitrogen atmosphere at room temperature, the solvent was removed in vacuo and the residue was dissolved in chloroform, then adsorbed onto silica gel and loaded onto a silica gel column. The product was eluted using an ethyl acetate/hexanes gradient. Fractions containing pure product (as judged by TLC) were pooled and concentrated in vacuo to give 6.5 g (75%) of 2-cyano-5-(bromomethyl)thiophene.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe product was eluted
  4. additionFractions containing pure product (as judged by TLC)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-69104add2a2849aba17decff43b8a344
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726159

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