Potassium Iodide → 1,3,5-Trichloro-2-iodobenzene

HRID 1039350Notes

Reaction equation

HRID 1039350 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:13][C:14]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[C:15]=1N.N([O-])=O.[Na+].[I-:27].[K+].C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[Cl:13][C:14]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[C:15]=1[I:27]

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 124712,4,6-TrichloroanilineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23668193Sodium Nitrite

Product 1

HCID 2320541,3,5-Trichloro-2-iodobenzeneYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
12.5 °C

Procedure

To a solution of paratoluene sulfonic acid monohydrate (14.5 g; 76.4 mmol) in acetonitrile (100 ml) was added the 2,4,6-trichloroaniline (5.0 g; 25.5 mmol). The resulting white suspension was cooled to 10-15° C. and to this was added, gradually a solution of sodium nitrite (3.5 g; 51.0 mmol) and potassium iodide (10.6 g; 63.6 mmol) in water (15 ml), the suspension became dark brown, thick and gas release was observed. The thick mixture was stirred for 10 min at 10° C. and then temperature was allowed to increase to 20° C. The solution obtained was stirred for 1 h. The solution was poured in water, 1M sodium hydrogen carbonate solution was added (pH adjusted to 9-10) and 2M solution of sodium thiosulfate was added. The mixture was extracted three times with dichloromethane. Organics were combined, dried over sodium sulfate and the solvent was removed in vacuo to provide a resin which was subject to flash column chromatography (eluant: c-hexane). 6.3 g (80% of theory) of 1,3,5-trichloro-2-iodo-benzene was obtained as a white solid.

Workup

  1. additionto this was added
  2. temperatureto increase to 20° C
  3. customThe solution obtained
  4. stirringwas stirred for 1 h
  5. additionwas added
  6. extractionThe mixture was extracted three times with dichloromethane
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was removed in vacuo
  9. customto provide a resin which

Sources & evidence

ORD record
ord-0d7cddccfedf433282ac65485686e53b
Source dataset
uspto-grants-2013_10
Patent number
US08552049B2

Reaction notes

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