Hexane → 2-Bromo-1-(3,4-dichlorophenyl)propan-1-one

HRID 1399534Notes

Reaction equation

HRID 1399534 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:12])[CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[Br:13]Br.CCCCCC>C(Cl)Cl.BrBr>[Br:13][CH:10]([CH3:11])[C:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)=[O:12]

Participants

6

Reactant 3

HCID 8058HexaneHCID 24408Bromine2×HCID 5995981-(3,4-Dichlorophenyl)-1-propanone

Product 1

HCID 134353622-Bromo-1-(3,4-dichlorophenyl)propan-1-oneYield 100%

Reagents, catalysts & solvents 2

HCID 24408BromineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3′,4′-dichloropropiophenone (81, 5.02 g, 0.247 mol) in CH2Cl2 (100 mL) was added ten drops of bromine. After stirring at room temperature under nitrogen for several min, the characteristic red color of bromine disappeared indicating initiation of the reaction. The remainder of the bromine (1.27 mL, 24.7 mmol) was added dropwise and the reaction solution was allowed to stir at room temperature under nitrogen atmosphere for 1.75 h. Analysis by TLC (silica, 2:1 hexane:CH2Cl2) indicated consumption of starting material. The reaction solution was quenched and brought to a pH of 9 with a saturated aqueous solution of NaHCO3 and concentrated NH4OH. The solution was extracted with CH2Cl2, dried (Na2SO4), filtered, concentrated, and dried to give 7.14 g (100%) of 2-bromo-(3′,4′-dichlorophenyl)propan-1-one as a white solid. Characterization data is similar with data reported in Anderson, W. K.; Jones, A. N., J. Med. Chem. 1984, 27, (12), 1559-1565.

Workup

  1. custominitiation of the reaction
  2. stirringto stir at room temperature under nitrogen atmosphere for 1.75 h
  3. customconsumption of starting material
  4. customThe reaction solution was quenched
  5. extractionThe solution was extracted with CH2Cl2
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried

Sources & evidence

ORD record
ord-a965d1b780774807af87bc2f0ee82c06
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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