Reacción #607494

Ecuación de reacción

aluminum trichloride

DCE

144b

4-bromo-2-fluorobenzoyl chloride

DCE

→

1-(4-bromo-2-fluorophenyl)-3-chloropropan-1-one

Rendimiento 68.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroEthylene gas was bubbled through the dark suspension for 3 h until the acid chloride
2. 2
   Otrowas consumed
3. 3
   Temperaturacooled to 0° C.
4. 4
   Otroquenched with 4M HCl (500 mL)
5. 5
   OtroThe organic phase was separated
6. 6
   Lavadowashed with brine (100 mL)
7. 7
   Secadodried over anhydrous sodium sulfate
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe crude residue was purified by column chromatography (PE/EA=30 to 10:1)

Procedimiento

To a stirred suspension of aluminum trichloride (153 g, 1.15 mol) in DCE (1000 mL) was added a solution of 144b (271 g, 1.14 mol) in DCE (1000 mL) at 0° C. See FIG. 3. Ethylene gas was bubbled through the dark suspension for 3 h until the acid chloride was consumed. The reaction mixture was then stirred at RT overnight, cooled to 0° C., and quenched with 4M HCl (500 mL). The organic phase was separated and washed with brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude residue was purified by column chromatography (PE/EA=30 to 10:1) to give 1-(4-bromo-2-fluorophenyl)-3-chloropropan-1-one 144c (210 g, 68%).

Fuente