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

HRID 1419644Notes

Reaction equation

HRID 1419644 reaction equation
Cl[CH2:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1N.[ClH:10].N([O-])=O.[Na+].[I-:15].[K+]>O.C1CCCCC1>[Cl:10][C:6]1[CH:4]=[C:3]([CH3:2])[CH:9]=[CH:8][C:7]=1[I:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 109430152-ChloromethylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 27576182-Chloro-1-iodo-4-methylbenzeneYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8078CyclohexaneSolvent

Conditions

Temperature
-5 °C

Procedure

A stirred mixture of 2-chloromethylaniline (25.00 g, 0.177 mol) and 36% hydrochloric acid is warmed gently to obtain a solution, then cooled to -5° C. and a solution of sodium nitrite (13.45 g, 0.195 mol) in water is added dropwise whilst maintaining the temperature at -5° C. The mixture is stirred at 0° C. for 30 minutes, 100 ml of cyclohexane is added and a solution of potassium iodide (58.77 g, 0.354 mol) in water is added dropwise at a temperature of between 0° and 5° C. The mixture is stirred at room temperature (overnight for convenience) and the product is extracted into ether (×2). The combined organic extracts are washed with sodium metabisulphite, 10% sodium hydroxide, water and dried (MgSO4). The solvent is in vacuo to yield 35.0 g (87%) off-white solid.

Workup

  1. temperatureis warmed gently
  2. customto obtain a solution
  3. temperaturewhilst maintaining the temperature at -5° C
  4. stirringThe mixture is stirred at room temperature (overnight for convenience)
  5. extractionthe product is extracted into ether (×2)
  6. washThe combined organic extracts are washed with sodium metabisulphite, 10% sodium hydroxide, water
  7. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-1c0074ec601b4e64aa63cb3095123401
Source dataset
uspto-grants-1999_03
Patent number
US05888421

Reaction notes

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