p-Fluoronitrobenzene → Cyclopropyl(4-nitrophenyl)sulfane

HRID 1027842Notes

Reaction equation

HRID 1027842 reaction equation
[H-].[Na+].[CH:3]1([SH:6])[CH2:5][CH2:4]1.F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1>C1COCC1.O>[CH:3]1([S:6][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 4713099Cyclopropanethiol

Product 1

HCID 59252683Cyclopropyl(4-nitrophenyl)sulfaneYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.78 g (44.6 mmol) of sodium hydride (60%) was added in portions to a solution of 3.00 g (40.5 mmol) of cyclopropane thiol (preparation according to: E. Block et al., J. Am. Chem. Soc. 1992, 114, 3492) in 100 ml THF/100 ml diethyl ether and was stirred for 30 minutes at room temperature. Then 6.00 g (38.7 mmol) of 1-fluoro-4-nitrobenzene was added in portions. The mixture was stirred for 2 hours at 40° C. After it had cooled, the mixture was put in water and was extracted with benzene (3×). The combined organic phases were concentrated by evaporation and the residue was purified chromatographically (hexane/ethyl acetate 95:5). 4.6 g (23.6 mmol; yield: 61%) of the product was obtained.

Workup

  1. stirringThe mixture was stirred for 2 hours at 40° C
  2. temperatureAfter it had cooled
  3. extractionwas extracted with benzene (3×)
  4. concentrationThe combined organic phases were concentrated by evaporation
  5. customthe residue was purified chromatographically (hexane/ethyl acetate 95:5)
  6. custom4.6 g (23.6 mmol; yield: 61%) of the product was obtained

Sources & evidence

ORD record
ord-607fc493f2ea4baab620b947d6b7bf3b
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

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