Water → 1-(Ethylsulfanyl)-4-nitrobenzene

HRID 383734Notes

Reaction equation

HRID 383734 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].I[CH2:14][CH3:15].O>CCO>[CH2:14]([S:12][C:9]1[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1)[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 158094-Nitrobenzenethiol

Product 1

HCID 123213391-(Ethylsulfanyl)-4-nitrobenzeneYield 59.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of NaOH (0.13 g, 3.2 mmol) in EtOH (10 mL) was added 4-nitrothiophenol (0.50 g, 3.2 mmol) and iodoethane (0.26 mL, 3.2 mmol). After stirring 2 h the reaction mixture was added to water (30 mL) and extracted with Et2O (3×25 mL). The combined extracts were washed with satd NH4Cl (3×25 mL) and brine, dried (MgSO4) and concentrated under reduced pressure. The crude material was chromatographed (silica, EtOAc/Hex 0:100 to 30:70) to yield 1-ethylthio-4-nitrobenzene (0.35 g, 59%) as a yellow crystalline solid. 1H-NMR (CDCl3) δ 8.13 (2H, d, J=8.8), 7.32 (2H, d, J=8.8), 3.06 (2H, q, J=7.3), 1.41 (3H, t, J=7.3). The title compound was prepared from 1-ethylthio-4-nitrobenzene in a manner similar to that described in Example 3A: MS (ESI): 419 (MH+).

Workup

  1. extractionextracted with Et2O (3×25 mL)
  2. washThe combined extracts were washed with satd NH4Cl (3×25 mL) and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was chromatographed (silica, EtOAc/Hex 0:100 to 30:70)

Sources & evidence

ORD record
ord-267d12c57f494b67b36893f2f7744db6
Source dataset
uspto-grants-2013_02
Patent number
US08367667B2

Reaction notes

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