Acetic Acid → 4'-Bromo-3-chloropropiophenone

HRID 2084549Notes

Reaction equation

HRID 2084549 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12]([OH:15])(=O)[CH3:13].[CH2:16](Cl)[Cl:17]>>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:15])[CH2:13][CH2:16][Cl:17])=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6344Dichloromethane3×HCID 7961BromobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 957904'-Bromo-3-chloropropiophenone

Procedure

45.3 g of aluminium chloride are stirred at room temperature in 80 ml of CH2Cl2. Maintaining vigorous stirring, a solution of β-propionic acid chloride (38.09 g, 28.7 ml, 0.3 mol) is poured slowly into 20 ml of CH2Cl2. The CH2Cl2-AlCl3-acid chloride complex forms quickly and the solution turns dark red. A solution of bromobenzene (47.1 g, 31.6 ml, 0.3 mol) is then introduced dropwise into 20 ml of CH2Cl2. The solution is then stirred for 15 hours at room temperature. The mixture is hydrolysed over 190 g of ice, to which 7.6 ml of concentrated acetic acid have been added. The organic phase is washed neutral and the solvent is removed by evaporation under reduced pressure. A dark red oil is obtained, from which the title compound is obtained in the form of a yellowish solid by extraction while hot with petroleum ether.

Workup

  1. temperatureMaintaining vigorous stirring
  2. additionhave been added
  3. washThe organic phase is washed neutral
  4. customthe solvent is removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b73e44bacae148178e6e18404f159493
Source dataset
uspto-grants-2004_04
Patent number
US06716852B2

Reaction notes

Loading…