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

HRID 1087179Notes

Reaction equation

HRID 1087179 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[S-:4].[K+].Cl[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22]>CN(C)C=O.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[S:4][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 2

HCID 795964'-Chloro-3'-nitroacetophenoneHCID 23700122Potassium 2,4-difluorothiophenoxide

Product 1

HCID 85674884'-(2,4-Difluorophenylthio)-3'-nitroacetophenoneYield 95.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of potassium 2,4-difluorothiophenoxide (5.5 g) in N,N-dimethylformamide (9 ml) was added dropwise to a solution of 4'-chloro-3'-nitroacetophenone (5 g) in toluene (50 ml). The mixture was stirred at room temperature for 2 hours, washed with water, dried and evaporated to dryness. The residue was washed with a mixture of hexane and ethanol to give crystals of 4'-(2,4-difluorophenylthio)-3'-nitroacetophenone (7.4 g).

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated to dryness
  4. washThe residue was washed with a mixture of hexane and ethanol

Sources & evidence

ORD record
ord-186dc326c8d0430e8867bc6f291ecc91
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

Loading…