Réaction #2198

ord-39af67312f5442e6ae004f66e6de33ad

Équation de réaction

O=C(c1ccc(Cl)cc1)c1ccc(CBr)cc1
4-bromomethyl-4'-chlorobenzophenone
N#C[S-].[Na+]
sodium thiocyanate
CCO
ethanol
N#CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1
desired product
Rendement 42.0%
N#CSCc1ccc(C(=O)c2ccc(Cl)cc2)cc1
4-Chloro-4'-thiocyanatomethylbenzophenone
Rendement 42.0%

Conditions de réaction

Température
60°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    ConcentrationThe reaction mixture was concentrated
  2. 2
    workup.ADDITIONwater was added to the residue
  3. 3
    ExtractionThe mixture was extracted with ethyl acetate
  4. 4
    LavageThe ethyl acetate layer was washed with water
  5. 5
    Séchagedried over anhydrous magnesium sulfate
  6. 6
    workup.DISTILLATIONEthyl acetate was distilled off under reduced pressure
  7. 7
    LavageThe residual solid was washed with a solvent mixture of n-hexane

Mode opératoire

4-bromomethyl-4'-chlorobenzophenone (5.7 g) and sodium thiocyanate (5.5 g) were added to ethanol (50 ml), and the mixture was stirred for one hour at 60° C. The reaction mixture was concentrated, and water was added to the residue. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residual solid was washed with a solvent mixture of n-hexane:ethyl acetate=10:1 to obtain the desired product (2.2 g, melting point: 129° to 131° C., yield:42%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05728699uspto-grants-1998_03