1,2-Dichloroethane → 1-(4-Bromo-2-fluorophenyl)-3-chloro-1-propanone

HRID 520312Notes

Reaction equation

HRID 520312 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[C:8]([F:15])[CH:7]=1.[Cl:16][CH2:17][CH2:18]Cl>>[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](=[O:11])[CH2:18][CH2:17][Cl:16])=[C:8]([F:15])[CH:7]=1

Participants

4

Reactant 3

HCID 111,2-Dichloroethane2×HCID 27340264-Bromo-2-fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 594738271-(4-Bromo-2-fluorophenyl)-3-chloro-1-propanoneYield 68%

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%).

Workup

  1. customEthylene gas was bubbled through the dark suspension for 3 h until the acid chloride
  2. customwas consumed
  3. temperaturecooled to 0° C.
  4. customquenched with 4M HCl (500 mL)
  5. customThe organic phase was separated
  6. washwashed with brine (100 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude residue was purified by column chromatography (PE/EA=30 to 10:1)

Sources & evidence

ORD record
ord-9946ceff88c245b994c6a22182dd4693
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

Loading…