Benzyl Bromide → 1-(Benzylsulfonyl)-4-bromo-2-chlorobenzene

HRID 70578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70578
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([Cl:12])[CH:3]=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:24]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[Cl:12])(=[O:10])=[O:9])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

7

Edukt 4

HCID 7498Benzyl BromideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 27347664-Bromo-2-chlorobenzenesulfonyl chloride

Produkt 1

HCID 584525461-(Benzylsulfonyl)-4-bromo-2-chlorobenzeneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 4-bromo-2-chlorobenzenesulfonyl chloride (1.16 g), sodium sulfite (1.01 g) and sodium bicarbonate (672 mg) in water (8 mL) was stirred at 100° C. for 1.5 hours. The reaction solution was cooled to 50° C. and tetrabutylammonium bromide (1.29 g) and benzyl bromide (1.43 mL) were added, after which the mixture was stirred at 70° C. for further three hours. The reaction solution was cooled to room temperature and water was added, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the title compound as a white solid (1.29 g, 94%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-79a6fae59ea343e4a8161c43b77776bf
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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