Water → Cyclopropyl(4-nitrophenyl)sulfane

HRID 2403557Notes

Reaction equation

HRID 2403557 reaction equation
[CH:1]1([SH:4])[CH2:3][CH2:2]1.[H-].[Na+].F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.O>C1COCC1.C(OCC)C>[CH:1]1([S:4][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 4713099Cyclopropanethiol

Product 1

HCID 59252683Cyclopropyl(4-nitrophenyl)sulfaneYield 61%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

A 4% strength solution of 3.00 g (40.5 mmol) of cyclopropanethiol (preparation according to: E. Block et al., J. Am. Chem. Soc. 1992, 114, 3492) in THF/diethyl ether (1:1) was admixed in portions with 1.78 g (44.6 mmol) of sodium hydride (60%) and stirred for 30 minutes at room temperature. The portionwise addition of 6.00 g (38.7 mmol) of 1-fluoro-4-nitrobenzene was then carried out. The mixture was stirred at 40° C. for 2 hours. After cooling, the mixture was added to water and extracted (3×) with benzene. The combined organic phases were concentrated by evaporation and the residue was purified chromatographically (hexane/ethyl acetate 95:5). This gave 4.6 g (23.6 mmol; yield: 61%) of the product.

Workup

  1. stirringThe mixture was stirred at 40° C. for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted (3×) with benzene
  4. concentrationThe combined organic phases were concentrated by evaporation
  5. customthe residue was purified chromatographically (hexane/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-815fa7ceaed34a02bd7fe91b638dd6d0
Source dataset
uspto-grants-2014_08
Patent number
US08802686B2

Reaction notes

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