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

HRID 1597

Reaction equation

HRID 1597 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-69104add2a2849aba17decff43b8a344
Source dataset
uspto-grants-1998_03
Patent number
US05726159

Linked notes

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