Iodine → 4-Bromo-2-iodo-6-nitroaniline

HRID 1941917

Reaction equation

HRID 1941917 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[I:12]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+].[Ag+]>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:6])=[C:7]([I:12])[CH:8]=1

Participants

5

Reactant 2

HCID 807IodineHCID 701324-Bromo-2-nitroaniline

Product 1

HCID 106887094-Bromo-2-iodo-6-nitroanilineYield 88%

Reagents, catalysts & solvents 2

HCID 159865Silver sulfateCatalystHCID 702EthanolSolvent

Procedure

4-Bromo-2-nitroaniline (14.3 g, 0.0659 mol) was added in one portion to iodine (17.6 g, 0.0692 mol) dissolved in ethanol (300 ml), followed by silver (I) sulphate (20.4 g 0.0659 mol). After stirring at ambient temperature for 18 hours the reaction was filtered and the solid obtained was washed with dichloromethane until all the orange product had dissolved. The combined filtrates were evaporated in vacuo and the resulting solid was washed with diethyl ether/40-60 Petroleum ether (1:1) and filtered to give 4-bromo-2-iodo-6-nitroaniline as an orange solid (19.8 g, 88%), which was used without further purification.

Workup

  1. filtrationwas filtered
  2. customthe solid obtained
  3. washwas washed with dichloromethane until all the orange product
  4. dissolutionhad dissolved
  5. customThe combined filtrates were evaporated in vacuo
  6. washthe resulting solid was washed with diethyl ether/40-60 Petroleum ether (1:1)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-54557a36fd9448bfb384bda60fb8b6b2
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Linked notes

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