Iodine → 4-Amino-3-iodobenzonitrile

HRID 925328Notes

Reaction equation

HRID 925328 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

4-amino-3-iodobenzonitrile was prepared according to method D Step I with Iodine (0.645 g; 2.54 mmol), silver sulphate (0.791 g; 2.54 mmol) and 4-aminobenzonitrile (0.300 g; 2.54 mmol) in ethanol (10 mL). The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to yield 0.222 g (36%) of 4-amino-3-iodobenzonitrile as a white solid.

Workup

  1. custom4-amino-3-iodobenzonitrile was prepared
  2. customThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-79487ae7d95b4c1b9636bc0754fe2c4a
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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