Hydrochloric Acid → 4-Chloro-2-fluoro-5-methoxybenzaldehyde

HRID 849965Notes

Reaction equation

HRID 849965 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F: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:1][C:2]1[C:3]([O:10][CH3:11])=[CH:4][C:5]([CH:12]=[O:13])=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723810Sodium FormateHCID 226256071-Chloro-5-fluoro-4-iodo-2-methoxybenzene

Product 1

HCID 149282684-Chloro-2-fluoro-5-methoxybenzaldehydeYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 36.3 g of 2-chloro-4-fluoro-5-iodo-1-methoxybenzene, 12.9 g of sodium formate, 1.78 g of dichlorobis(triphenylphosphine) palladium, and 113 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 hydrochloric acid, 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 7.09 g (yield, 30%) of 4-chloro-2-fluoro-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-43c7107112214bd38503012d6044da09
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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