Iodine → 4-Amino-3-iodobenzonitrile

HRID 58634Notes

Reaction equation

HRID 58634 reaction equation
[I:1]I.[NH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[NH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[I:1]

Participants

5

Reactant 2

HCID 807IodineHCID 133964-Aminobenzonitrile

Product 1

HCID 44163954-Amino-3-iodobenzonitrileYield 36%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

Iodine (0.645 g; 2.54 mmol) was added to a stirred mixture of silver sulphate (0.791 g; 2.54 mmol) and 4-aminobenzonitrile (0.300 g; 2.54 mmol) in ethanol (10 mL). The reaction mixture was stirred at room temperature for 18 hours and filtered over celite. The volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium thiosulphate. The organic layer was washed with brine, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to afford 0.222 g (36%) of the title compound as a white solid.

Workup

  1. filtrationfiltered over celite
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6fb95214d0204cd4a5a60e3b3432e379
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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