Water → HCID 378891, compound

HRID 1356540Notes

Reaction equation

HRID 1356540 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-d9120c611d324be18818224bc924fc24
Source dataset
uspto-grants-2003_07
Patent number
US06586592B2

Reaction notes

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