Water → HCID 12074226, compound

HRID 1356546Notes

Reaction equation

HRID 1356546 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].F[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].O>C(#N)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([S:8][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[N+:23]([O-:25])=[O:24])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 677672,5-DifluoronitrobenzeneHCID 75710m-Fluorobenzenethiol

Product 1

HCID 12074226HCID 12074226, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-fluorothiophenol (8.36 g, 65.2 mmol) and potassium carbonate (9.81 g, 71.0 mmol) in 115 mL of dry acetonitrile is added 2,5-difluoronitrobenzene (7.00 mL, 64.55 mmol). The mixture is allowed to stir at room temperature for 2 hours. Water and CH2Cl2 (120 mL each) are added and the layers separated. The aqueous layer is extracted with CH2Cl2 (3×50 mL). The combined organics are dried over MgSO4, filtered, and concentrated to give a bright yellow solid. The solid is triturated with hexane to give 17.1 g (99%) of the title compound as a bright yellow solid.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer is extracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe combined organics are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a bright yellow solid
  7. customThe solid is triturated with hexane

Sources & evidence

ORD record
ord-3ec86ff17c2c4f3e8a502f0c8f54f949
Source dataset
uspto-grants-2003_07
Patent number
US06586592B2

Reaction notes

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