Potassium Iodide → 2-Iodo-5-nitrotoluene

HRID 1428757Notes

Reaction equation

HRID 1428757 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1N.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N([O-])=O.[Na+].[I-:28].[K+]>C(#N)C.O.C(OCC)(=O)C>[I:28][C:3]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=1[CH3:1]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 74412-Methyl-4-nitroanilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 23668193Sodium Nitrite

Product 1

HCID 792252-Iodo-5-nitrotolueneYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-methyl-4-nitroaniline (500 mg, 3.286 mmol) in acetonitrile and water were added p-toluenesulfonic acid monohydrate (1.875 g, 9.858 mmol), sodium nitrite (453 mg, 6.572 mmol) and potassium iodide (1.363 g, 8.215 mmol). The reaction mixture was stirred for 4 h at room temperature. The mixture dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give 1-iodo-2-methyl-4-nitrobenzene (812 mg, 94%).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-fd741eb11a644c3db8e17eef77b1538f
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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