Water → 3-(Methylthio)-4-nitrophenol

HRID 658464Notes

Reaction equation

HRID 658464 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 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-fluoro-4-nitrophenol (3.0 g, 19.1 mmol) in anhydrous DMF (100 mL) was added dropwise sodium thiomethoxide (2.57 mL, 38.2 mmol, 2.0 eq) followed by potassium carbonate (7.92 g, 57.3 mmol, 3.0 eq), and the reaction mixture was stirred at RT for 18 h. Water was then added to quench the solution, and the reaction mixture was extracted with EtOAc (3×250 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, and evaporated under reduced pressure. Purification of the crude using MPLC (biotage) eluted with 20% EtOAc—hexanes afforded 3.25 g (91.9%) of 3-(methylsulfanyl)4-nitrophenol as a yellow solid.

Workup

  1. customto quench the solution
  2. extractionthe reaction mixture was extracted with EtOAc (3×250 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customPurification of the crude
  7. washeluted with 20% EtOAc—hexanes

Sources & evidence

ORD record
ord-c0d6c3ff153a4f0882a5e81eec7bc60a
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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