1-(3-Chloro-4-nitrophenyl)ethanone → 3'-(2,4-Difluorophenylthio)-4'-nitroacetophenone

HRID 1087192Notes

Reaction equation

HRID 1087192 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[F:14][C:15]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:16]=1[S-:17].[K+]>C1(C)C(C)=CC=CC=1>[F:14][C:15]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:16]=1[S:17][C:2]1[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 104427551-(3-Chloro-4-nitrophenyl)ethanoneHCID 23700122Potassium 2,4-difluorothiophenoxide

Product 1

HCID 102448083'-(2,4-Difluorophenylthio)-4'-nitroacetophenoneYield 61.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 3'-chloro-4'-nitroacetophenone (2.4 g), potassium 2,4-difluorothiophenoxide (2.7 g), and N,Ndimethylformamide (5 ml) in xylene (50 ml) was stirred for 8 hours at room temperature. The mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residual solid was recrystallized from ethanol to give prisms of 3'-(2,4-difluorophenylthio)-4'-nitroacetophenone (2.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residual solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-32a801e5fbff4ed1a50c02c93b95d056
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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