Hydrochloric Acid → 4-Chloro-3-iodophenol

Participants

Reaction Steps

To a solution of 1-chloro-2-iodo-4-methoxybenzene (2.68 g, 10.0 mmol) in dichloromethane (20 ml) was dropped under ice cooling 0.91M boron tribromide in dichloromethane (13.0 ml, 12.0 mmol). The mixture was stirred for 1 hour under ice cooling and for a day at room temperature. To the reaction mixture was added an aqueous saturated sodium hydrogencarbonate solution. The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution and dried over sodium sulfate. The solvent was removed to give the subject compound as pale brown crystals (2.61 g, quantitatively).

Provenance & Evidence