Water → 3-(Methylthio)-4-nitrophenol

HRID 658464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658464
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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 441857023-(Methylthio)-4-nitrophenolAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c0d6c3ff153a4f0882a5e81eec7bc60a
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076488B2

Notizen zur Reaktion

Wird geladen…