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

HRID 1952842Notes

Reaction equation

HRID 1952842 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 80%

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 refluxed for 8 h. The solvent was removed in a rotary evaporator at 40° C., and the residue was suspended in ethyl acetate and transferred into a Soxleth [sic] apparatus. The residue was extracted overnight, the yellow solution was dried over sodium sulfate and concentrated in a rotary evaporator, and the resulting yellow solid was recrystallized from ether to result in 25.3 g of product (80% of theory).

Workup

  1. temperaturerefluxed for 8 h
  2. customThe solvent was removed in a rotary evaporator at 40° C.
  3. extractionThe residue was extracted overnight
  4. dry with materialthe yellow solution was dried over sodium sulfate
  5. concentrationconcentrated in a rotary evaporator
  6. customthe resulting yellow solid was recrystallized from ether

Sources & evidence

ORD record
ord-73e1d0cd1fdd46fa8d8f05c8a3f13d43
Source dataset
uspto-grants-2000_09
Patent number
US06114358

Reaction notes

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