Carbon tetrabromide → 4-(Bromomethyl)thiophene-2-carbonitrile

HRID 1582898Notes

Reaction equation

HRID 1582898 reaction equation
[C:1]([C:3]1[S:4][CH:5]=[C:6]([CH2:8]O)[CH:7]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:29]C(Br)(Br)Br>C1COCC1>[Br:29][CH2:8][C:6]1[CH:7]=[C:3]([C:1]#[N:2])[S:4][CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 106542884-(Hydroxymethyl)thiophene-2-carbonitrile

Product 1

HCID 107506074-(Bromomethyl)thiophene-2-carbonitrileYield 110.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

11.7 g (84.07 mmol) of 2-cyano-4-hydroxymethylthiophene together with 24.1 g (91.87 mmol) of triphenylphosphine were dissolved in 100 ml of-THF at room temperature, and 30.47 g (91.87 mmol) of tetrabromomethane were added, a little at a time, with cooling (ice bath). After stirring for 3 hours at room temperature, the mixture was concentrated in vacuo and purified by chromatography over silica gel (methylene chloride/petroleum ether). 18.8 g of crystalline pale yellow product which still contained petroleum ether resulted.

Workup

  1. temperaturea little at a time, with cooling (ice bath)
  2. concentrationthe mixture was concentrated in vacuo
  3. custompurified by chromatography over silica gel (methylene chloride/petroleum ether)

Sources & evidence

ORD record
ord-47c262f819a24678a702bcf6f034475f
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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