Iodine → 1-Benzyl-4-bromobenzene

Participants

Reaction Conditions

Reaction Steps

4-Bromodiphenylmethane was prepared as shown in Scheme 3. 4-Bromobenzhydrol in a 3-neck flask equipped with a reflux condenser and a thermometer was mixed with 500 ml of acetic acid, 113 g (445 mmol) of iodine and 226 ml, 50 wt. % of phosphorous acid (2.2 mol). The reaction mixture was heated at 80° C. for 24 hours and then cooled. 700 ml of ice-water was added to the reaction mixture and the reaction mixture was extracted with hexane (200 ml) 5 times. The combined organic layer was washed with 10 wt. % KOH solution and 200 ml of a saturated ammonium chloride solution and then further washed with a saturated Na2SO3 solution twice. The solvent was evaporated and the result product was dried under vacuum to provide a yield of 61% (276 mmol). BP: 103° C. (5*10−2 mbar)

Provenance & Evidence