Sulfuric Acid → 1-Chloro-3-iodo-5-nitrobenzene

HRID 326643Notes

Reaction equation

HRID 326643 reaction equation
[Cl:1][C:2]1[C:8]([N+]([O-])=O)=[CH:7][C:5](N)=[C:4]([I:12])[CH:3]=1.S(=O)(=O)(O)O.[N:18]([O-:20])=[O:19].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([I:12])[CH:5]=[C:7]([N+:18]([O-:20])=[O:19])[CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 15739203HCID 15739203, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 197351701-Chloro-3-iodo-5-nitrobenzeneYield 42.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-2-iodo-5-nitroaniline (8.5 g) in ethanol (38 ml) was added concentrated sulphuric acid (4.4 ml) dropwise, then the solution was heated to reflux and solid sodium nitrite (4.9 g) added in small amounts over 30 minutes. The mixture was refluxed a further one hour and poured into ice water, the product extracted into ethyl acetate, washed with water and brine and the organic layer was dried over sodium sulfate. The solution was evaporated and the residue purified by column chromatography to give 5-chloro-3-iodonitrobenzene (3.4 g). δ (360 MHz, DMSO-d6) 8.28 (1H, d, 2-H), 8.35 (1H, d, 6-H) and 8.46 (1H, d, 4-H).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed a further one hour
  4. extractionthe product extracted into ethyl acetate
  5. washwashed with water and brine
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. customThe solution was evaporated
  8. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-d12b293ebc7d45f99707c434da6840af
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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