Water → Cyclopropyl(4-nitrophenyl)sulfane

HRID 2199508Notes

Reaction equation

HRID 2199508 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

Cyclopropanethiol in THF/diethyl ether was admixed in portions with sodium hydride and stirred at room temperature. 1-Fluoro-4-nitrobenzene was then added in portions. The mixture was stirred for 2 hours at 40° C. After cooling, the mixture was added to water and extracted with benzene (3×). The combined organic phases were concentrated by evaporation and the residue was purified by chromatography (hexane/acetic ester 95:5). (Yield: 61%).

Workup

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

Sources & evidence

ORD record
ord-6003621cd878488d9bf9186795deb4d9
Source dataset
uspto-grants-2016_06
Patent number
US09359306B2

Reaction notes

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