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

HRID 726665

Reaktionsgleichung

Reaktionsgleichung von HRID 726665
[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-8b3dc7b9f8934c6c9909ec4403960098
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05710130

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