Hydrochloric Acid → HCID 21200443, compound

HRID 1870781Notes

Reaction equation

HRID 1870781 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5](I)=[CH:4][C:3]=1[O:10][CH:11]([CH3:13])[CH3:12].[CH:14]([O-])=[O:15].[Na+].Cl>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:4][C:5]([CH:14]=[O:15])=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723810Sodium FormateHCID 21200442HCID 21200442, compound

Product 1

HCID 21200443HCID 21200443, compoundYield 34.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Then, 62.9 g of 2-chloro-4-fluoro-5-iodo-1-isopropoxybenzene, 20.4 g of sodium formate, and 2.81 g of dichlorobis(triphenylphosphine)palladium were dissolved in 120 ml of N,N-dimethylformamide, which was stirred at 90° to 100° C. for 12 hours, while bubbling carbon monoxide thereinto. After completion of the reaction, the reaction mixture was cooled to room temperature, to which diluted hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 15 g of 4-chloro-2-fluoro-5-isopropoxybenzaldehyde.

Workup

  1. customwhile bubbling carbon monoxide
  2. customAfter completion of the reaction
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cd8eb0c83abe4bfc84f57781bb2dd4d2
Source dataset
uspto-grants-2000_08
Patent number
US06100257

Reaction notes

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