p-Fluoronitrobenzene → 1-(Cyclopentylsulfanyl)-4-nitrobenzene

HRID 2101669Notes

Reaction equation

HRID 2101669 reaction equation
[CH:1]1([SH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1>C(#N)C.O>[CH:1]1([S:6][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 15510Cyclopentanethiol

Product 1

HCID 129583181-(Cyclopentylsulfanyl)-4-nitrobenzeneYield 32.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Cyclopentanethiol (1.0 g) (available from Aldrich) was dissolved in acetonitrile (10 ml) and potassium carbonate (1.35 g) was added. After 5 min, 1-fluoro-4-nitrobenzene (1.38 g) (available from Aldrich) was added and the mixture was stirred at room temperature overnight. The mixture was diluted with water and extracted with ether. The organic layer was washed with 1M aqueous sodium hydroxide (20 ml), water (20 ml), and 1M aqueous hydrochoric acid (20 ml). The organic layer was separated and the solvent evaporated in vacuo to give the title compound as a yellow liquid (0.7 g).

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with 1M aqueous sodium hydroxide (20 ml), water (20 ml), and 1M aqueous hydrochoric acid (20 ml)
  3. customThe organic layer was separated
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-1e674ae55e9242639f423ebf918190a0
Source dataset
uspto-grants-2009_08
Patent number
US07572915B2

Reaction notes

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