Reaction #12060

Reaction equation

benzyl magnesium chloride

2-bromo-indene

→

2-benzylindene

Solvents

ether

diethyl ether

—

hexanes

Conditions

Workup

1. 1
   TemperatureThe reaction was heated
2. 2
   Temperatureto reflux overnight
3. 3
   Otherquenched
4. 4
   workup.ADDITIONadding 150 mL of 1.0 M aqueous hydrochloric acid
5. 5
   OtherThe organic layer was separated
6. 6
   Washwashed twice with 50 mL of ether
7. 7
   Dryingdried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Otherthe volatiles removed in vacuo
10. 10
    Otherto leave a dark oil
11. 11
    Otherpurified by flash column chromatography

Procedure

A 500 mL 3 neck flask was charged with 2.5 g (13 mmol) of 2-bromo-indene, 50 mg of NiCl2(1,3-bis(diphenylphosphino)propane) (0.06 mmol) and 150 mL of diethyl ether. To this mixture was added dropwise 12.8 mL of 1.0 M benzyl magnesium chloride in ether (12.8 mmol). The reaction was heated to reflux overnight and then quenched by cooling to 0° C. and adding 150 mL of 1.0 M aqueous hydrochloric acid. The organic layer was separated and washed twice with 50 mL of ether. The organic extracts were combined, dried over magnesium sulfate, filtered and the volatiles removed in vacuo to leave a dark oil. The sample was dissolved in a small amount of hexanes and purified by flash column chromatography using silica and hexanes as the elutent. Yield: 1.75 g, 66 percent

Source