Water → 4-Chloro-2-iodo-6-methylbenzoic acid

HRID 2427669Notes

Reaction equation

HRID 2427669 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[I:12]NC(=O)CCC(N)=O.O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([C:6]([OH:8])=[O:7])=[C:9]([I:12])[CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3482694-Chloro-2-methylbenzoic acidHCID 21864724N-Iodosuccinamide

Product 1

HCID 671931174-Chloro-2-iodo-6-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-2-methyl-benzoic acid (3.40 g, 20 mmol,), N-iodosuccinamide (4.4 g, 22 mmol) and palladium (II) acetate (0.448 g, 2 mmol) in dry DMF (35 mL) was heated at 100° C. for 36 h under nitrogen atmosphere. After this time, the reaction mixture was cooled to ambient temperature and poured into water. The aqueous solution was extracted with ethyl acetate (2×100 mL) and the combined organic extracts were washed with aqueous sodium thiosulphate (30 mL) and brine (30 mL). The organic solution was dried over anhydrous MgSO4, filtered and concentrated to afford 4-chloro-2-iodo-6-methyl-benzoic acid. The product was used without further purification.

Workup

  1. temperatureAfter this time, the reaction mixture was cooled to ambient temperature
  2. extractionThe aqueous solution was extracted with ethyl acetate (2×100 mL)
  3. washthe combined organic extracts were washed with aqueous sodium thiosulphate (30 mL) and brine (30 mL)
  4. dry with materialThe organic solution was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b2dba51477024fbaae11a6612b9f4162
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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