Potassium Carbonate → 4',4-Dichlorochalcone

HRID 2379305

Reaction equation

HRID 2379305 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14]S(F)(=O)=O)=[CH:10][CH:9]=1.[Cl:19][C:20]1[CH:29]=[CH:28][C:23]([C:24](=[O:27])[CH2:25]Br)=[CH:22][CH:21]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl:19][C:20]1[CH:29]=[CH:28][C:23]([C:24](=[O:27])/[CH:25]=[CH:14]/[C:11]2[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromideHCID 18958404HCID 18958404, compound

Product 1

HCID 53770114',4-DichlorochalconeYield 68.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A catalytic amount (about 300 mg) of tetrabutylammonium bromide and 68 g of powdered anydrous potassium carbonate were added to a solution of 21.8 g 4-chlorophenylmethanesulphonyl fluoride and 23.3 g of 4-chlorophenacyl bromide in 200 ml of tetrahydrofuran at room temperature, while stirring. The mixture was stirred for a further 8 hours at 50° C. The reaction mixture was allowed to cool down to room temperature and was then filtered to remove inorganic substances which had precipitated. The organic phase was concentrated by stripping off the solvent under reduced pressure. The residue was recrystallized from ethanol. In this manner, 19.0 g of trans-1,3-di-(4-chlorophenyl)-prop-2-en-1-one were obtained in the form of yellow crystals of melting point 156° C.

Workup

  1. stirringThe mixture was stirred for a further 8 hours at 50° C
  2. filtrationwas then filtered
  3. customto remove inorganic substances which
  4. customhad precipitated
  5. concentrationThe organic phase was concentrated
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-8d838e072ffe4b74bc4706278c196e33
Source dataset
uspto-grants-1994_11
Patent number
US05360935

Linked notes

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