3-Iodo-4,5-dimethoxybenzaldehyde → 5-Formyl-2,3-dimethoxybenzonitrile

HRID 1684045Notes

Reaction equation

HRID 1684045 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9](I)[C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[Cu](C#N)[C:15]#[N:16]>CN(C=O)C>[C:15]([C:9]1[C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([CH:8]=1)[CH:6]=[O:7])#[N:16]

Participants

4

Reactant 2

HCID 27781133-Iodo-4,5-dimethoxybenzaldehydeHCID 178418260HCID 178418260, compound

Product 1

HCID 190418105-Formyl-2,3-dimethoxybenzonitrileYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4-dimethoxy-5-iodobenzaldehyde (41) (FIG. 22) (4.40 g, 15.07 mmole), copper cyanide (13.5 g, 150.7 mmole) and dry DMF (45 ml) were stirred under an argon atmosphere for 18 hours at 140° C. The reaction was cooled to room temperature, filtered through celite, and the filtrate concentrated to an oil in vacuo. The dark brown oil was purified through a short flash silica column using 11 hexane/ethyl acetate as eluent to yield 2.87 g (69%) of a white solid.

Workup

  1. filtrationfiltered through celite
  2. concentrationthe filtrate concentrated to an oil in vacuo
  3. customThe dark brown oil was purified through a short flash silica column

Sources & evidence

ORD record
ord-eac5e564155d40ff8b11c2c14a6f59c4
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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