Reaction #607494

Reaction equation

aluminum trichloride

DCE

144b

4-bromo-2-fluorobenzoyl chloride

DCE

→

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

Yield 68.0%

Conditions

Workup

1. 1
   OtherEthylene gas was bubbled through the dark suspension for 3 h until the acid chloride
2. 2
   Otherwas consumed
3. 3
   Temperaturecooled to 0° C.
4. 4
   Otherquenched with 4M HCl (500 mL)
5. 5
   OtherThe organic phase was separated
6. 6
   Washwashed with brine (100 mL)
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   OtherThe crude residue was purified by column chromatography (PE/EA=30 to 10:1)

Procedure

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%).

Source