Sulfur Dioxide → 2,6-Dimethylbiphenyl-4-sulfonyl chloride

HRID 252246

Reaktionsgleichung

Reaktionsgleichung von HRID 252246
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]([CH3:20])[CH:8]=1.S(=O)=O.[S:24](Cl)([Cl:27])(=[O:26])=[O:25]>O1CCCC1.CCCCCC>[CH3:13][C:11]1[CH:12]=[C:7]([S:24]([Cl:27])(=[O:26])=[O:25])[CH:8]=[C:9]([CH3:20])[C:10]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 4

HCID 1119Sulfur DioxideHCID 24648Sulfuryl chlorideHCID 668578334-Bromo-2,6-dimethylbiphenylHCID 178418339Butyllithium

Produkt 1

HCID 866167172,6-Dimethylbiphenyl-4-sulfonyl chlorideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

2.5 M n-butyllithium, in tetrahydrofuran, (0.46 ml, 1.17 mmol, 1.1 equiv.) was added dropwise to a solution of 4-bromo-2,6-dimethylbiphenyl (0.28 g, 1.06 mmol, 1.0 equiv.) in dry tetrahydrofuran (5 ml), under nitrogen at −78° C. and the mixture stirred for 15 minutes. This solution was added, by canula, to a solution of sulfur dioxide (3 mL) and tetrahydrofuran (3 ml) under nitrogen at −78° C. The solution was allowed to warm to room temperature while stirring for 16 hours. The solvent was evaporated under reduced pressure and the residue suspended in hexane (4 ml) and dichloromethane (4 ml). The suspension was cooled to 0° C., a solution of sulfuryl chloride (0.14 g, 1.06 mmol, 1.0 equiv.) in hexane (2 ml) was added and the mixture was allowed to warm to room temperature while stirring for 1.5 hours. The hexane and dichloromethane were evaporated under reduced pressure to afford crude 2,6-dimethylbiphenyl-4-sulfonyl chloride, 0.22 g (74% yield) as a red gum, this material was used in the next step without further purification.

Aufarbeitung

  1. stirringwhile stirring for 16 hours
  2. customThe solvent was evaporated under reduced pressure
  3. temperatureThe suspension was cooled to 0° C.
  4. temperatureto warm to room temperature
  5. stirringwhile stirring for 1.5 hours
  6. customThe hexane and dichloromethane were evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-01e64ea572504516919410a0628684f0
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868030B2

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