Acetic Acid → 4-Bromo-2-fluoro-1-(methylsulfonyl)benzene

HRID 216716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216716
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[C:4]([F:10])[CH:3]=1.CC(O)=[O:13].OO.C([O-])(O)=O.[Na+].[OH2:22]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:9])(=[O:13])=[O:22])=[C:4]([F:10])[CH:3]=1

Komponenten

6

Edukt 5

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 516892Sodium BicarbonateHCID 219340644-Bromo-2-fluorothioanisole

Produkt 1

HCID 459337204-Bromo-2-fluoro-1-(methylsulfonyl)benzene

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a 50 ml sealable tube is introduced 4-Bromo-2-fluoro-1-methylsulfanyl-benzene (as obtained in preparation 63, 5 g, 22.6 mmol) followed by 4.6 ml AcOH. 9.3 ml of a 30% H2O2 solution in H2O is added at RT. The tube is sealed and the resulting colorless biphasic solution is stirred at 100° C. for 2 h. After cooling, the pH of the medium is set basic with solid NaHCO3 and then extracted with CH2Cl2 several times. The combined organic layers are washed with brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo. The title compound is obtained as a colorless solid, Rt=0.916 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min)

Aufarbeitung

  1. customThe tube is sealed
  2. temperatureAfter cooling
  3. extractionextracted with CH2Cl2 several times
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-115fefd5d8484e3fb8343ab8fc635417
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193189B2

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