Water → 3-(Methylthio)-4-nitrophenol

HRID 1035388Notes

Reaction equation

HRID 1035388 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) were 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 RT 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.

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-0e2ec14933ce48e9b2d98d2094375696
Source dataset
uspto-grants-2013_10
Patent number
US08546387B2

Reaction notes

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