Dimethylformamide → 5-Bromo-1,3-dimethyl-2-(methylsulfanyl)benzene

HRID 732833

Reaktionsgleichung

Reaktionsgleichung von HRID 732833
[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5](F)=[C:6]([CH3:8])[CH:7]=1.CN(C)C=O.[CH3:16][S-:17].[Na+]>O.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([S:17][CH3:16])=[C:6]([CH3:8])[CH:7]=1

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 27362985-Bromo-2-fluoro-1,3-dimethylbenzeneHCID 4378561Sodium methanethiolate

Produkt 1

HCID 685195015-Bromo-1,3-dimethyl-2-(methylsulfanyl)benzeneAusbeute 14,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Add 5-bromo-2-fluoro-1,3-dimethyl-benzene (3.5 g, 17.2 mmol) to dimethylformamide (DMF, 30 mL) at ambient temperature followed by sodium thiomethoxide (1.32 g, 17.9 mmol). Heat at 50° C. for 8 hours and dilute with water (10 mL) and diethyl ether (100 mL). Separate the layers, wash the organics with brine, and dry with magnesium sulfate before concentrating to a residue. Chromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane to give 566 mg (14%) of 5-bromo-1,3-dimethyl-2-methylsulfanyl-benzene.

Aufarbeitung

  1. customSeparate the layers
  2. washwash the organics with brine
  3. dry with materialdry with magnesium sulfate
  4. concentrationbefore concentrating to a residue
  5. washChromatograph the residue on a SiO2 column eluting with diethyl ether (20%) in hexane

Quellen und Nachweise

ORD-Eintrag
ord-13edda37ddd44583938f634527cac803
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585977B2

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