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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence