Reaction #1135810

ord-1752b023ff794165bdd789db60ee326f

Reaction equation

O=C(CBr)c1ccc(Br)cc1F
1-(4-bromo-2-fluorophenyl)-2-bromo-1-ethanone
N#C[S-].[NH4+]
ammonium thiocyanate
O=C([O-])O.[Na+]
sodium bicarbonate
N#CSCC(=O)c1ccc(Br)cc1F
1-(4-bromo-2-fluorophenyl)-2-thiocyanato-1-ethanone

Solvents

Conditions

Temperature
25°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherTo the reaction mixtures
  2. 2
    Extractionthe mixtures were extracted with ethyl acetate
  3. 3
    WashThe organic layers were washed with aqueous saturated sodium bicarbonate solution
  4. 4
    Dryingwere dried over anhydrous sodium sulfate
  5. 5
    ConcentrationThe resulting mixtures were concentrated under reduced pressure

Procedure

A mixture of the above-mentioned 1-(4-bromo-2-fluorophenyl)-2-bromo-1-ethanone, ammonium thiocyanate 2.15 g and acetonitrile 100 mL was stirred at 25° C. for one hour. To the reaction mixtures was added aqueous saturated sodium bicarbonate solution and the mixtures were extracted with ethyl acetate. The organic layers were washed with aqueous saturated sodium bicarbonate solution and were dried over anhydrous sodium sulfate. The resulting mixtures were concentrated under reduced pressure to give 1-(4-bromo-2-fluorophenyl)-2-thiocyanato-1-ethanone.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09380782B2uspto-grants-2016_07