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

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.

1. customIn a 50 ml three-neck flask equipped
2. temperaturecooling funnel
3. stirringThe resulting suspension is stirred for 15 min at ambient temperature
4. additionwas added dropwise over a period of 25 minutes
5. additionDuring the exothermic addition
6. custombubbling
7. stirringThe mixture was stirred at 40° C. for 1 hour
8. distillationThe volatiles were distilled off at 55° C.
9. washwashed with water (20 ml)
10. extractionThe aqueous phase was extracted with an additional portion of dichloromethane (30 ml)
11. concentrationThe combined organic phases were then concentrated under reduced pressure

ORD record

ord-b65d8a50437f49fc9f9915d27455f25c

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051272B2