Water → HCID 378891, compound

HRID 1369396Notes

Reaction equation

HRID 1369396 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].F[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].O>C(#N)C.C(Cl)Cl>[F:21][C:18]1[CH:19]=[CH:20][C:15]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:16]([N+:22]([O-:24])=[O:23])[CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 677672,5-Difluoronitrobenzene

Product 1

HCID 378891HCID 378891, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of thiophenol (0.96 mL, 9.3 mmol) and potassium carbonate (1.4 g, 10.1 mmol) in 16 mL of dry acetonitrile is added 2,5-difluoronitrobenzene (1.0 mL, 9.2 mmol). The mixture is allowed to stir overnight at rt. Water (30 mL) and CH2Cl2 are added and the layers seperated. The aqueous layer is extracted with CH2Cl2 (3×25 mL). The combined organics are dried over MgSO4, filtered, and concentrated. Recrystallization from EtOAc/heptane gives 2.3 g (99%) of the title compound as a solid, mp 66-67° C.

Workup

  1. customthe layers seperated
  2. extractionThe aqueous layer is extracted with CH2Cl2 (3×25 mL)
  3. dry with materialThe combined organics are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customRecrystallization from EtOAc/heptane

Sources & evidence

ORD record
ord-955093c441384f5faaa1dac0108c9cbe
Source dataset
uspto-grants-2003_06
Patent number
US06579870B2

Reaction notes

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