Oxalyl chloride → HCID 58385804, compound

HRID 1038345Notes

Reaction equation

HRID 1038345 reaction equation
[C:1](Cl)(=O)[C:2](Cl)=O.[Br:7][C:8]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:9]=1[C:10]([OH:12])=O>ClCCl.CN(C=O)C>[Br:7][C:8]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:9]=1[C:10]([C:8]1[CH:16]=[CH:15][C:14]([CH2:1][CH3:2])=[CH:13][CH:9]=1)=[O:12]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27355722-Bromo-5-iodobenzoic acid

Product 1

HCID 58385804HCID 58385804, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (9.5 mL) is added to a solution of 2-bromo-5-iodo-benzoic acid (25.0 g) in dichloromethane (50 mL). A few drops of DMF are added and the mixture is stirred at room temperature overnight. Then, the reaction solution is concentrated under reduced pressure and the residue is taken up in dichloromethane (50 mL) and ethylbenzene (23 mL). The resulting solution is cooled in an ice-bath and aluminum trichloride (12.5 g) is added in portions. Then, the cooling bath is removed and the reaction mixture is stirred at room temperature for 4 h. After consumption of the intermediate substituted benzoyl chloride, the reaction mixture is poured onto crushed ice and the organic phase is separated off. The aqueous phase is extracted with ethyl acetate and the combined organic phases are washed in succession with 1 M hydrochloric acid, 1 M potassium hydroxide solution and brine. The organic phase is dried (sodium sulphate) and the solvent is removed under reduced pressure to give the product as an oil that crystallizes on standing.

Workup

  1. concentrationThen, the reaction solution is concentrated under reduced pressure
  2. temperatureThe resulting solution is cooled in an ice-bath
  3. additionaluminum trichloride (12.5 g) is added in portions
  4. customThen, the cooling bath is removed
  5. stirringthe reaction mixture is stirred at room temperature for 4 h
  6. customAfter consumption of the intermediate substituted benzoyl chloride
  7. additionthe reaction mixture is poured
  8. customonto crushed ice
  9. customthe organic phase is separated off
  10. extractionThe aqueous phase is extracted with ethyl acetate
  11. washthe combined organic phases are washed in succession with 1 M hydrochloric acid, 1 M potassium hydroxide solution and brine
  12. dry with materialThe organic phase is dried (sodium sulphate)
  13. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-1d1f6738cfb14db9b6a318d1afad7338
Source dataset
uspto-grants-2013_10
Patent number
US08551957B2

Reaction notes

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