Isopropenyl acetate → 1-(4-Bromo-2,6-dichloro-phenyl)-propan-2-one

In a 50 ml three-neck flask equipped with mechanical stirring, cooling funnel, dropping funnel and thermometer under nitrogen at ambient temperature filled with acetonitrile (10 ml), were added cuprous oxide (1.5 g, 0.018 mol), isopropenyl acetate (13.6 ml, 0.125 mol) and tert-butyl nitrite (1.7 ml, 0.0125 mol). The resulting red suspension is stirred for 15 min at ambient temperature. A solution of 4-bromo-2,6-dichloroaniline (2.0 g, 0.0083 mol), dissolved in acetonitrile (15 ml) was added dropwise over a period of 20 minutes. During the addition, bubbling was observed. The mixture was stirred at 40° C. for 20 hours. The red crude mixture was passed through celite to remove solid particles and concentrated under reduce pressure to give a brown solid. The residue was dissolved in dichloromethane (120 ml) and washed with water (2×50 ml) and brine (40 ml). Organics were dried over sodium sulfate and concentrated under reduced pressure to give crude 1-(4-bromo-2,6-dichloro-phenyl)-propan-2-one (2.3 g) as a dark brown oil.

1. customIn a 50 ml three-neck flask equipped with mechanical stirring
2. temperaturecooling funnel
3. additionwas added dropwise over a period of 20 minutes
4. additionDuring the addition
5. custombubbling
6. stirringThe mixture was stirred at 40° C. for 20 hours
7. customto remove solid particles
8. concentrationconcentrated
9. customto give a brown solid
10. washwashed with water (2×50 ml) and brine (40 ml)
11. dry with materialOrganics were dried over sodium sulfate
12. concentrationconcentrated under reduced pressure

ORDレコード

ord-d465b97e93df426daec3f002eebba67b

出典データセット

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09073839B2