3-Chloro-4-nitrobenzonitrile → 3-(2,4-Difluorophenylthio)-4-nitrobenzonitrile

HRID 1087172Notes

Reaction equation

HRID 1087172 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:13]=[C:14]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[C:15]#[N:16]>CO.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:18]1[CH:17]=[C:14]([CH:13]=[CH:12][C:19]=1[N+:20]([O-:22])=[O:21])[C:15]#[N:16]

Participants

5

Reactant 2

HCID 149730283-Chloro-4-nitrobenzonitrileHCID 23700122Potassium 2,4-difluorothiophenoxide

Product 1

HCID 102663153-(2,4-Difluorophenylthio)-4-nitrobenzonitrileYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of potassium 2,4-difluorothiophenoxide (6.1 g) in methanol (30 ml) was added dropwise to a solution of 3-chloro-4-nitrobenzonitrile (5 g) in toluene (50 ml). The mixture was stirred for 5 hours at room temperature, washed with water, and concentrated to dryness. The oily residue was crystallized from a mixture of ethanol and hexane to give crystals of 3-(2,4-difluorophenylthio)-4-nitrobenzonitrile (3.6 g).

Workup

  1. washwashed with water
  2. concentrationconcentrated to dryness
  3. customThe oily residue was crystallized from a mixture of ethanol and hexane

Sources & evidence

ORD record
ord-42b2c14492a64d459b4064115dd98e6e
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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