Bromoacetic Acid → 1,2,4-Trifluoro-5-(methylsulfonyl)benzene

HRID 20554

Reaktionsgleichung

Reaktionsgleichung von HRID 20554
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].S([O-])([O-])=O.[Na+].[Na+].[C:20](=O)(O)[O-].[Na+].BrCC(O)=O>O>[F:9][C:5]1[CH:4]=[C:3]([S:10]([CH3:20])(=[O:12])=[O:11])[C:2]([F:1])=[CH:7][C:6]=1[F:8]

Komponenten

6

Edukt 4

HCID 6227Bromoacetic AcidHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 27769792,4,5-Trifluorobenzenesulfonyl chloride

Produkt 1

HCID 467393961,2,4-Trifluoro-5-(methylsulfonyl)benzeneAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

2,4,5-Trifluorophenyl sulfonyl chloride (279 mg) was added to a solution of sodium sulfite (306 mg) and sodium bicarbonate (153 mg) in water (4 mL). The mixture was heated to 150° C. in a sealed microwave vial for 400 seconds and allowed to cool. The mixture was treated with bromoacetic acid (253 mg) in water (1 mL), and heated to 150° C. for 300 seconds then allowed to cool, following which the precipitate was removed by filtration and dried in vacuo to give the desired compound (169 mg). The material was used without further purification. 1H NMR δ (d6-DMSO): 3.35 (s, 3H), 7.87-8.01 (m, 2H).

Aufarbeitung

  1. temperatureto cool
  2. temperatureheated to 150° C. for 300 seconds
  3. temperatureto cool
  4. customwas removed by filtration
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e9d217611dd942d58da602e9cc758320
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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