2',4'-Dichloroacetophenone → 2-Bromo-1-(2,4-dichlorophenyl)ethan-1-one

HRID 1533117Notes

Reaction equation

HRID 1533117 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[Al+3].[Cl-].[Cl-].[Cl-].[Br:16]Br>CCOCC>[Br:16][CH2:10][C:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])=[O:11]

Participants

5

Reactant 3

HCID 166932',4'-DichloroacetophenoneHCID 24408Bromine2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 758282-Bromo-1-(2,4-dichlorophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

25 g (0.1322 mol) of 2′,4′-dichloroacetophenone was placed in a three-neck round bottom flask equipped with a magnetic stir bar, reflux condenser, and dropping funnel. Anhydrous ether (30 mL) and AlCl3 (0.20 g) were added. The solution was stoppered and cooled to 0° C. in an ice bath. Br2 (21.13 g, 0.1322 mol) was added dropwise (at a rate of approximately 0.5 mL/min). After addition of Br2 was complete, HBr and the solvent were removed under reduced pressure. The remaining HBr was removed by blowing a stream of nitrogen over the orange oily product. The resulting oil was placed under high vacuum until all the bubbling had ceased. The product was obtained as a viscous orange oil, which solidified upon standing in the refrigerator. Yield: 35.72 g (100%); TLC: 95% Hexanes/5% Acetone, Rf=0.35.

Workup

  1. customequipped with a magnetic stir bar
  2. temperaturereflux condenser
  3. customHBr and the solvent were removed under reduced pressure
  4. customThe remaining HBr was removed
  5. customThe product was obtained as a viscous orange oil, which

Sources & evidence

ORD record
ord-be001c5cdd144f3cb80be2884de1f961
Source dataset
uspto-grants-2001_03
Patent number
US06207695B1

Reaction notes

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