Dimethylformamide → HCID 58385804, compound

HRID 1664102Notes

Reaction equation

HRID 1664102 reaction equation
[C:1](Cl)(=O)[C:2](Cl)=O.CN(C)C=O.[Br:12][C:13]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:14]=1[C:15]([OH:17])=O>ClCCl>[Br:12][C:13]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:14]=1[C:15]([C:13]1[CH:21]=[CH:20][C:19]([CH2:1][CH3:2])=[CH:18][CH:14]=1)=[O:17]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27355722-Bromo-5-iodobenzoic acid

Product 1

HCID 58385804HCID 58385804, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (9 mL) and dimethylformamide (0.5 mL) are added to a mixture of 2-bromo-5-iodo-benzoic acid (25 g) in dichloromethane (80 ml). The reaction mixture is stirred for 14 h at room temperature, then filtered and separated from all volatile constituents in a rotary evaporator. The residue is dissolved in dichloromethane (50 mL) and ethyl-benzene (23 mL) and the resultant solution is cooled to −5° C. Then aluminum trichloride (12.5 g) is added batchwise so that the temperature maintains below 10° C. The solution is warmed slowly to room temperature and stirred overnight. The solution is poured onto crushed ice, the organic phase is separated, and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with hydrochloric acid (1 mol/l), sodium hydroxide solution (1 mol/l) and with brine. The organic phase is dried over sodium sulphate and the solvent is removed to give the product as an oil that crystallizes on standing.

Workup

  1. filtrationfiltered
  2. customseparated from all volatile constituents in a rotary evaporator
  3. dissolutionThe residue is dissolved in dichloromethane (50 mL)
  4. temperatureethyl-benzene (23 mL) and the resultant solution is cooled to −5° C
  5. additionThen aluminum trichloride (12.5 g) is added batchwise so that the temperature
  6. custommaintains below 10° C
  7. temperatureThe solution is warmed slowly to room temperature
  8. stirringstirred overnight
  9. additionThe solution is poured
  10. customonto crushed ice
  11. customthe organic phase is separated
  12. extractionthe aqueous phase is extracted with ethyl acetate
  13. washThe combined organic phases are washed with hydrochloric acid (1 mol/l), sodium hydroxide solution (1 mol/l) and with brine
  14. dry with materialThe organic phase is dried over sodium sulphate
  15. customthe solvent is removed

Sources & evidence

ORD record
ord-dba3a4d268534e5b9c75317ff412483a
Source dataset
uspto-grants-2011_10
Patent number
US08039441B2

Reaction notes

Loading…