Isopropenyl acetate → 1-(2,4,6-Trichlorophenyl)-2-propanone

Participants

Reaction Steps

In a 50 ml three-neck flask equipped with stirring, cooling funnel, dropping funnel and thermometer under nitrogen at ambient temperature filled with acetonitrile (20 ml), isopropenyl acetate (31 g, 0.31 mol) and tert-amyl nitrite (3.6 g, 0.031 mol). The resulting suspension is stirred for 15 min at ambient temperature. A solution of 2,4,6-trichloroaniline (4.0 g, 0.020 mol), dissolved in acetonitrile (20 ml) was added dropwise over a period of 25 minutes. During the exothermic addition, bubbling was observed. The mixture was stirred at 40° C. for 1 hour. The volatiles were distilled off at 55° C. and 11 mbar. The residue was taken up with dichloromethane (50 ml) and washed with water (20 ml). The aqueous phase was extracted with an additional portion of dichloromethane (30 ml). The combined organic phases were then concentrated under reduced pressure to give a crude 1-(4-bromo-2,6-dichloro-phenyl)-propan-2-one (6.7 g, 34.8% GC; 48% yield) as a dark brown oil.

Provenance & Evidence