Water → 3-(Methylthio)-4-nitrophenol

HRID 1864666Notes

Reaction equation

HRID 1864666 reaction equation
F[C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:12][S-:13].[Na+].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:12][S:13][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenolHCID 4378561Sodium methanethiolate

Product 1

HCID 441857023-(Methylthio)-4-nitrophenolYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-fluoro-4-nitrophenol (2 g, 12.7 mmol) in dry DMF (67 mL) was added, by aliquots, 2 equivalents of sodium thiomethoxide (1.78 g, 25.5 mmol) followed by 3 equivalents of potassium carbonate (5.27 g, 38.2 mmol). The mixture was stirred at room temperature for 23 hours and then water (100 mL) was added. The mixture was extracted with EtOAc, and the combined organic layers washed successively with water (60 mL) and brine (60 mL) and then dried over MgSO4. The solvent was evaporated under vacuum to provide the title compound (2.12 g, 90%) as a yellow powder. 1H-NMR (δ, ppm, DMSO-d6): 2.44 (s, 3H, HMe), 6.72 (d, 1H, Harom 6, J6-5=9.0 Hz), 6.79 (s, 1H, Harom 2), 8.19 (d, 1H, Harom 5, J5-8=9.1 Hz), 11.20 (broad s, 1H, OH).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe combined organic layers washed successively with water (60 mL) and brine (60 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-b5a76c8177b54b0ca67cddc23d3b0a89
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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