Reaktion #940373

Reaktionsgleichung

para-toluenesulfonic acid

p-Tolyl magnesium bromide

6-bromo-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one

Compound 3

6-bromo-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one

Water

→

title compound

Ausbeute 65.0%

7-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydro-naphthalene

Ausbeute 65.0%

Lösungsmittel

dichloromethane

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture was quenched with water at 0° C.
2. 2
   Extraktionextracted with diethyl ether (3×5 mL)
3. 3
   Waschenwashed with brine (1×5 mL)
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated at reduced pressure
6. 6
   Sonstigeto give a light yellow oil
7. 7
   Waschenthe organic layer was washed with brine (1×5 mL)
8. 8
   Trocknendried (MgSO4)
9. 9
   Einengenconcentrated at reduced pressure
10. 10
    SonstigePurification by flash chromatography (hexane)

Vorschrift

p-Tolyl magnesium bromide (1 M solution in diethyl ether, 4.2 mL, 4.17 mmol) was added slowly to a solution of 6-bromo-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound 3, 350 mg, 1.39 mmol) in 10 mL of diethyl ether at 0° C. After stirring and warming to room temperature for 2 h, the mixture was quenched with water at 0° C., extracted with diethyl ether (3×5 mL), washed with brine (1×5 mL), dried (MgSO4) and concentrated at reduced pressure to give a light yellow oil. The crude oil was then dissolved in 10 mL of dichloromethane and stirred with 100 mg of para-toluenesulfonic acid at room temperature for 2 h. Water (10 mL) was then added and the organic layer was washed with brine (1×5 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (hexane) gave the title compound (295 mg, 65% yield) as a colorless oil:

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