Hydrochloric Acid → 2-Chloro-1-iodo-4-methylbenzene

HRID 343963

Reaction equation

HRID 343963 reaction equation
Cl.N[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[Cl:10].N([O-])=O.[Na+].[I-:15].[K+]>O>[Cl:10][C:4]1[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=1[I:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 120072-Chloro-p-toluidine2×HCID 23668193Sodium Nitrite

Product 1

HCID 27576182-Chloro-1-iodo-4-methylbenzeneYield 111.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-2 °C

Procedure

250 ml of concentrated hydrochloric acid and 75 g of 4-amino-3-chlorotoluene (0.53 mol) are introduced onto 166 g of ice, and a solution of 40.3 g of sodium nitrite (0.583 mol) in 170 ml of water is then added dropwise at 0° C. After the solution has been stirred for 15 minutes, it is filtered through glass wool, and the solution, which has been cooled to -2° C., is added dropwise to a solution, warmed to room temperature, of 455 g of potassium iodide (2.74 mol) in 1 l of water together with a batch prepared analogously with 0.30 mol of 4-amino-3-chloro-toluene. After the reaction mixture has been stirred overnight, it is extracted three times with ether and the combined organic phases are washed twice with dilute sodium hydroxide solution, twice with dilute sodium bisulphite solution and with water. After drying over sodium sulphate, filtration and concentration, the residue of copper powder is distilled over a Vigreux column under 1 mm Hg. The fraction between 70° and 85° C. gives 149 g of a yellow oil [7% of theory, Rf =0.57 (hexane:ethyl acetate=9:1)].

Workup

  1. filtrationit is filtered through glass wool
  2. additionis added dropwise to a solution
  3. stirringAfter the reaction mixture has been stirred overnight
  4. extractionit is extracted three times with ether
  5. washthe combined organic phases are washed twice with dilute sodium hydroxide solution, twice with dilute sodium bisulphite solution and with water
  6. dry with materialAfter drying over sodium sulphate, filtration and concentration
  7. distillationthe residue of copper powder is distilled over a Vigreux column under 1 mm Hg

Sources & evidence

ORD record
ord-3eb9687e7e2a4671962df837c2482c46
Source dataset
uspto-grants-1999_01
Patent number
US05863930

Linked notes

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