6-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide → 6-Bromo-2,2,3-trimethyl-2,3-dihydro-1-benzothiophene-3-ol 1,1-dioxide

HRID 2390296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2390296
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6](=[O:13])[C:7]([CH3:12])([CH3:11])[S:8](=[O:10])(=[O:9])[C:4]=2[CH:3]=1.[CH3:16][Mg]Br>CCOCC>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]([CH3:16])([OH:13])[C:7]([CH3:11])([CH3:12])[S:8](=[O:9])(=[O:10])[C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 565941096-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide2×HCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 565941126-Bromo-2,2,3-trimethyl-2,3-dihydro-1-benzothiophene-3-ol 1,1-dioxideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A cooled (0° C.) solution of 6-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide (Intermediate 241; 750 mg; 2.59 mmol) in anhydrous Et2O (22.5 ml) was treated carefully with a 3 M solution of methylmagnesium bromide in Et2O (2.6 ml; 7.8 mmol). The white solution was stirred at RT for 1.5 before being quenched with a saturated solution of NH4Cl in water. The phases were separated and the aqueous phase was extracted with Et2O. The combined organic phases were washed with water and brine, dried over anhydrous magnesium sulfate and concentrated to dryness to afford the title compound as a white solid (767 mg, 97%).

Aufarbeitung

  1. custombefore being quenched with a saturated solution of NH4Cl in water
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with Et2O
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-2d7b0e3609354945a7a45f2c4c77f6a5
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273769B2

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