Water → 4-Chloro-2-{[2-chloro-4-(ethylsulfonyl)phenyl]thio}-1-nitrobenzene

HRID 910834Notes

Reaction equation

HRID 910834 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[SH:13].C(=O)([O-])[O-].[K+].[K+].F[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29].O>CN(C=O)C>[Cl:27][C:25]1[CH:26]=[CH:21][C:22]([N+:28]([O-:30])=[O:29])=[C:23]([S:13][C:3]2[CH:4]=[CH:5][C:6]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[CH:7][C:2]=2[Cl:1])[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 673906392-Chloro-4-(ethylsulfonyl)benzenethiol

Product 1

HCID 673916204-Chloro-2-{[2-chloro-4-(ethylsulfonyl)phenyl]thio}-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from step (i) (1.60 g), potassium carbonate (0.934 g) and 2-fluoro-4-chloro-nitrobenzene (1.18 g) in DMF (20 ml) was stirred at RT overnight. Water (200 ml) was added and the mixture extracted with ethyl acetate. The organics were dried, evaporated under reduced and the residue purified by chromatography on silica eluting with isohexane/diethylether 4:1, yield 0.80 g.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. customThe organics were dried
  3. customevaporated
  4. customthe residue purified by chromatography on silica eluting with isohexane/diethylether 4:1, yield 0.80 g

Sources & evidence

ORD record
ord-270b8f60c6134d7aa5ec7dda45b671f4
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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