Reaktion #2445044

Reaktionsgleichung

HCl

PhMgBr

magnesium

bromobenzene

4-bromoindan-1-one

→

7-Bromo-3-phenyl-1H-indene

Lösungsmittel

water

ether

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThis mixture was stirred overnight at room temperature
2. 2
   TemperaturThe resulting mixture was cooled to 0° C.
3. 3
   SonstigeThe organic layer was separated
4. 4
   Extraktionand the aqueous layer was extracted with 2×200 ml of dichloromethane
5. 5
   ExtraktionThe combined extract
6. 6
   Trocknenwas dried over K2CO3
7. 7
   Sonstigeevaporated to dryness
8. 8
   SonstigeThe product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 65 mm, 400 mm, eluant:hexanes)
9. 9
   Sonstigerecrystallized from hexanes
10. 10
    SonstigeYield

Vorschrift

Under an argon atmosphere, to a solution of PhMgBr in THF [obtained from 7.60 g (0.312 mol) of magnesium turnings, 50.0 g (0.318 mmol) of bromobenzene, and 200 ml of THF], a solution of 43.9 g (0.208 mol) of 4-bromoindan-1-one in 400 ml of THF was added dropwise with vigorous stirring at −10° C. This mixture was stirred overnight at room temperature; and, then, 300 ml of ether was added. The resulting mixture was cooled to 0° C., and 200 ml of cold water and then 200 ml of 12 M HCl were added. The organic layer was separated; and the aqueous layer was extracted with 2×200 ml of dichloromethane. The combined extract was dried over K2CO3 and then evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 65 mm, 400 mm, eluant:hexanes) and then recrystallized from hexanes. Yield, 48.4 g (86%) of a white crystalline solid.

Quelle