4-Bromothiophene-2-carbaldehyde → 5-formylthiophene-3-carbonitrile

HRID 1582899Notes

Reaction equation

HRID 1582899 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.[Cu][C:10]#[N:11]>CN(C=O)C>[C:10]([C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1)#[N:11]

Participants

4

Reactant 2

HCID 877924-Bromothiophene-2-carbaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 122800095-formylthiophene-3-carbonitrileYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

49.3 g (258.05 mmol) of 4-bromothiophene-2-carbaldehyde and 27.8 g (310.41 mmol) of copper(I) cyanide were suspended in 130 ml of absolute DMF and the suspension was refluxed for 8 hours. The solvent was evaporated in vacuo in a rotary evaporator at 400C, the residue was suspended in ethyl acetate and the suspension was transferred into a Soxleth apparatus. The residue was extracted overnight, the yellow solution was dried over sodium sulfate and evaporated in vacuo in a rotary evaporator, and the resulting yellow solid was recrystallized frome ether. 25.3 g of product resulted (80% of theory).

Workup

  1. temperaturethe suspension was refluxed for 8 hours
  2. customThe solvent was evaporated in vacuo in a rotary evaporator at 400C
  3. extractionThe residue was extracted overnight
  4. dry with materialthe yellow solution was dried over sodium sulfate
  5. customevaporated in vacuo in a rotary evaporator
  6. customthe resulting yellow solid was recrystallized frome ether

Sources & evidence

ORD record
ord-1607e9ff987245b5bf0cf60badedb941
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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