Iodine → Ethyl 4-amino-2-chloro-5-iodobenzoate

HRID 339114

Reaction equation

HRID 339114 reaction equation
[I:1]I.[NH2:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([Cl:15])[CH:5]=1>C(O)C.S([O-])([O-])(=O)=O.[Ag+].[Ag+]>[NH2:3][C:4]1[C:14]([I:1])=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([Cl:15])[CH:5]=1

Participants

5

Reactant 2

HCID 807IodineHCID 13287887Ethyl 4-amino-2-chlorobenzoate

Product 1

HCID 58247958Ethyl 4-amino-2-chloro-5-iodobenzoate

Reagents, catalysts & solvents 2

HCID 159865Silver sulfateCatalystHCID 702EthanolSolvent

Procedure

An iodine solution in ethanol was admixed with silver(I) sulphate and ethyl 4-amino-2-chlorobenzoate and then stirred at room temperature for 45 min. The reaction mixture was filtered through a frit and the filtrate was concentrated under reduced pressure. The residue was slurried in EtOAc and admixed with dilute sodium hydrogencarbonate solution. Once everything had gone into solution, the aqueous phase was removed and sodium thiosulphate was dissolved therein. The organic phase was washed again with the aqueous phase, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated under reduced pressure. Column chromatography purification on silica gel with cyclohexane/ethyl acetate as the eluent (gradient from 10% ethyl acetate to 33% ethyl acetate).

Workup

  1. filtrationThe reaction mixture was filtered through a frit
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe aqueous phase was removed
  4. dissolutionsodium thiosulphate was dissolved
  5. washThe organic phase was washed again with the aqueous phase
  6. extractionthe aqueous phase was extracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customColumn chromatography purification on silica gel with cyclohexane/ethyl acetate as the eluent (gradient from 10% ethyl acetate to 33% ethyl acetate)

Sources & evidence

ORD record
ord-843454d3a09446a7bfa51292b6a62085
Source dataset
uspto-grants-2014_11
Patent number
US08889878B2

Linked notes

Loading…