Hydrochloric Acid → 2,4-Dichloro-5-methoxybenzaldehyde

HRID 849970Notes

Reaction equation

HRID 849970 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5](I)=[CH:4][C:3]=1[O:10][CH3:11].[CH:12]([O-])=[O:13].[Na+].Cl>CN(C)C=O>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([O:10][CH3:11])=[CH:4][C:5]=1[CH:12]=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723810Sodium FormateHCID 19365506HCID 19365506, compound

Product 1

HCID 193654912,4-Dichloro-5-methoxybenzaldehydeYield 44.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 22.6 g of 2,4-dichloro-5-iodo-1-methoxybenzene, 7.61 g of sodium formate, 1.05 g of dichlorobis(triphenylphosphine) palladium, and 60 ml of N,N-dimethylformamide was stirred, while bubbling carbon monoxide at 90° to 100° C. over 12 hours. After completion of the reaction, the reaction mixture was returned to room temperature, followed by dilution with diluted hydrochloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 6.75 g (yield, 44%) of 2,4-dichloro-5-methoxybenzaldehyde.

Workup

  1. customwhile bubbling carbon monoxide at 90° to 100° C. over 12 hours
  2. customAfter completion of the reaction
  3. customwas returned to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fdcd0bf28a2f448e9f9c2d7a4b389116
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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